PROCESS FOR MAKING HIV PROTEASE INHIBITORS
1. A process for forming a compound (I) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is C1-10 alkyl or aryl; comprising (a) reacting (A), (B), (C) and (D) to form a compound (F) wherein (A...
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| creator | ASKIN, DAVID SAGER, JESS, W ROSSEN, KAI VOLANTE, RALPH, P., REIDER, PAUL, J |
| description | 1. A process for forming a compound (I) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is C1-10 alkyl or aryl; comprising (a) reacting (A), (B), (C) and (D) to form a compound (F) wherein (A) is H2 N-(CH2)2-NHR where R is as defined above; (B) is selected from a halogenated acetaldehyde or a halogenated acetaldehyde C1-2 alkylacetal; (C) is R -CO2H where R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl; and (D) is R NC where R is as defined above; and (b) deblocking the compound (F) to form the compound (I) 2. A process for forming a compound (F) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl and R is C1-10 alkyl or aryl wherein comprising reacting an imine (C) with R NC in the presence of a carboxylic acid, R - CO2H, to form the compound (F) 3. The process of Claim 2, wherein the imine (C) is formed by reacting an ethylene diamine compound A of the formula H2N-(CH2)2-NHR with a halogenated acetaldehyde or a halogenated acetaldehyde di-C1-2 alkylacetal. 4. The process of Claim 2, wherein the compound (F) is prepared in one-pot without first isolating the imine (C) 5. The process of Claim 2, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 6. The process of Claim 5, wherein R is and R is t-butyl. 7. A process for forming a compound (J) comprising the steps of: 1) reacting a nitrile (H) where R is a group of formula with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form a compound of formula 2) resolving the racemic compound to isolate a compound 1 3) reacting the compound 1 with a compound 2 to form a compound 3 4) deblocking the compound 3 to form a compound J 8. A process for forming an amide (G) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; comprising reacting a nitrile (H) with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form the amide (G) 9. The process of Claim 8, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 10. The process of Claim 11, w |
| format | Patent |
| fullrecord | <record><control><sourceid>epo_EVB</sourceid><recordid>TN_cdi_epo_espacenet_EA000637B1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>EA000637B1</sourcerecordid><originalsourceid>FETCH-epo_espacenet_EA000637B13</originalsourceid><addsrcrecordid>eNrjZNAKCPJ3dg0OVnDzD1LwdfT29HNX8PAMUwAKh7g6BrsqePp5eDp5hvgHBfMwsKYl5hSn8kJpbgZ5N9cQZw_d1IL8-NTigsTk1LzUknhXRwMDAzNjcydDY8IqAMX5I70</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>patent</recordtype></control><display><type>patent</type><title>PROCESS FOR MAKING HIV PROTEASE INHIBITORS</title><source>esp@cenet</source><creator>ASKIN, DAVID ; SAGER, JESS, W ; ROSSEN, KAI ; VOLANTE, RALPH, P., REIDER, PAUL, J</creator><creatorcontrib>ASKIN, DAVID ; SAGER, JESS, W ; ROSSEN, KAI ; VOLANTE, RALPH, P., REIDER, PAUL, J</creatorcontrib><description>1. A process for forming a compound (I) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is C1-10 alkyl or aryl; comprising (a) reacting (A), (B), (C) and (D) to form a compound (F) wherein (A) is H2 N-(CH2)2-NHR where R is as defined above; (B) is selected from a halogenated acetaldehyde or a halogenated acetaldehyde C1-2 alkylacetal; (C) is R -CO2H where R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl; and (D) is R NC where R is as defined above; and (b) deblocking the compound (F) to form the compound (I) 2. A process for forming a compound (F) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl and R is C1-10 alkyl or aryl wherein comprising reacting an imine (C) with R NC in the presence of a carboxylic acid, R - CO2H, to form the compound (F) 3. The process of Claim 2, wherein the imine (C) is formed by reacting an ethylene diamine compound A of the formula H2N-(CH2)2-NHR with a halogenated acetaldehyde or a halogenated acetaldehyde di-C1-2 alkylacetal. 4. The process of Claim 2, wherein the compound (F) is prepared in one-pot without first isolating the imine (C) 5. The process of Claim 2, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 6. The process of Claim 5, wherein R is and R is t-butyl. 7. A process for forming a compound (J) comprising the steps of: 1) reacting a nitrile (H) where R is a group of formula with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form a compound of formula 2) resolving the racemic compound to isolate a compound 1 3) reacting the compound 1 with a compound 2 to form a compound 3 4) deblocking the compound 3 to form a compound J 8. A process for forming an amide (G) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; comprising reacting a nitrile (H) with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form the amide (G) 9. The process of Claim 8, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 10. The process of Claim 11, wherein R is 11. The process of Claim 10, wherein the strong acid is selected from H2S04, H3P04, CH3S03H or BF3. 12. The process of Claim 8, wherein the strong acid is H2S04. 13. The process of Claim 8, wherein the nitrile (H) is prepared by reacting an imine (C) with a cyanide ion to form the nitrile (H). 14. The process of Claim 13, wherein the imine (C) is prepared by reacting an ethylene diamine compound (A) of the formula H2N(CH2)2 NHR with a halogenated acetaldehyde or a halogenated acetaldehyde di-C1-2 alkylacetal. 15. The process of Claim 16, wherein preparation of nitrile (H) ' is accomplished in one-pot without first isolating the imine (C). 16. A compound of the formula (C) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl where said substituent is aryl or heteroaryl. 17. The compound of Claim 16, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 18. The compound of Claim 17, wherein R is 19. A compound of the formula (H) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl where said substituent is aryl or heteroaryl. 20. The compound of Claim 19, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 21. The compound of Claim 20, wherein R is 22. A process for forming an amide (G) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; comprising (a) reacting a compound (A), H2N-(CH2)2-NHR where R is as defined above, a compound (B) selected from a halogenated acetaldehyde or a halogenated acetaldehyde C1-2 alkylacetal and a cyanide ion to form a nitrile (H) (b) reacting the nitrile (H) with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form the amide (G) 23. A process for forming a compound (I) comprising the steps of: 1) reacting an imine (C) with R NC in the presence of carboxylic acid, R -CO2H to form a compound (F) where R is and R is t-butyl 2) deblocking the compound (F) to form the racemic compound (I) 3) resolving the racemic compound to isolate a compound 1 24. A process for forming a compound (J) comprising the steps of: 1) reacting imine (C) with R NC in the presence of carboxylic acid, R -CO2H to form the compound (F) where R is and R is t-butyl, 2) deblocking the compound (F) to form the racemic compound (I) 3) resolving the racemic compound to isolate a compound 1 4) reacting with compound 2 to form a compound 3 5) deblocking the compound 3 to form the compound (J).</description><edition>6</edition><language>eng ; rus</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>1999</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19991229&DB=EPODOC&CC=EA&NR=000637B1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25543,76293</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19991229&DB=EPODOC&CC=EA&NR=000637B1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>ASKIN, DAVID</creatorcontrib><creatorcontrib>SAGER, JESS, W</creatorcontrib><creatorcontrib>ROSSEN, KAI</creatorcontrib><creatorcontrib>VOLANTE, RALPH, P., REIDER, PAUL, J</creatorcontrib><title>PROCESS FOR MAKING HIV PROTEASE INHIBITORS</title><description>1. A process for forming a compound (I) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is C1-10 alkyl or aryl; comprising (a) reacting (A), (B), (C) and (D) to form a compound (F) wherein (A) is H2 N-(CH2)2-NHR where R is as defined above; (B) is selected from a halogenated acetaldehyde or a halogenated acetaldehyde C1-2 alkylacetal; (C) is R -CO2H where R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl; and (D) is R NC where R is as defined above; and (b) deblocking the compound (F) to form the compound (I) 2. A process for forming a compound (F) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl and R is C1-10 alkyl or aryl wherein comprising reacting an imine (C) with R NC in the presence of a carboxylic acid, R - CO2H, to form the compound (F) 3. The process of Claim 2, wherein the imine (C) is formed by reacting an ethylene diamine compound A of the formula H2N-(CH2)2-NHR with a halogenated acetaldehyde or a halogenated acetaldehyde di-C1-2 alkylacetal. 4. The process of Claim 2, wherein the compound (F) is prepared in one-pot without first isolating the imine (C) 5. The process of Claim 2, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 6. The process of Claim 5, wherein R is and R is t-butyl. 7. A process for forming a compound (J) comprising the steps of: 1) reacting a nitrile (H) where R is a group of formula with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form a compound of formula 2) resolving the racemic compound to isolate a compound 1 3) reacting the compound 1 with a compound 2 to form a compound 3 4) deblocking the compound 3 to form a compound J 8. A process for forming an amide (G) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; comprising reacting a nitrile (H) with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form the amide (G) 9. The process of Claim 8, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 10. The process of Claim 11, wherein R is 11. The process of Claim 10, wherein the strong acid is selected from H2S04, H3P04, CH3S03H or BF3. 12. The process of Claim 8, wherein the strong acid is H2S04. 13. The process of Claim 8, wherein the nitrile (H) is prepared by reacting an imine (C) with a cyanide ion to form the nitrile (H). 14. The process of Claim 13, wherein the imine (C) is prepared by reacting an ethylene diamine compound (A) of the formula H2N(CH2)2 NHR with a halogenated acetaldehyde or a halogenated acetaldehyde di-C1-2 alkylacetal. 15. The process of Claim 16, wherein preparation of nitrile (H) ' is accomplished in one-pot without first isolating the imine (C). 16. A compound of the formula (C) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl where said substituent is aryl or heteroaryl. 17. The compound of Claim 16, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 18. The compound of Claim 17, wherein R is 19. A compound of the formula (H) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl where said substituent is aryl or heteroaryl. 20. The compound of Claim 19, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 21. The compound of Claim 20, wherein R is 22. A process for forming an amide (G) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; comprising (a) reacting a compound (A), H2N-(CH2)2-NHR where R is as defined above, a compound (B) selected from a halogenated acetaldehyde or a halogenated acetaldehyde C1-2 alkylacetal and a cyanide ion to form a nitrile (H) (b) reacting the nitrile (H) with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form the amide (G) 23. A process for forming a compound (I) comprising the steps of: 1) reacting an imine (C) with R NC in the presence of carboxylic acid, R -CO2H to form a compound (F) where R is and R is t-butyl 2) deblocking the compound (F) to form the racemic compound (I) 3) resolving the racemic compound to isolate a compound 1 24. A process for forming a compound (J) comprising the steps of: 1) reacting imine (C) with R NC in the presence of carboxylic acid, R -CO2H to form the compound (F) where R is and R is t-butyl, 2) deblocking the compound (F) to form the racemic compound (I) 3) resolving the racemic compound to isolate a compound 1 4) reacting with compound 2 to form a compound 3 5) deblocking the compound 3 to form the compound (J).</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1999</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZNAKCPJ3dg0OVnDzD1LwdfT29HNX8PAMUwAKh7g6BrsqePp5eDp5hvgHBfMwsKYl5hSn8kJpbgZ5N9cQZw_d1IL8-NTigsTk1LzUknhXRwMDAzNjcydDY8IqAMX5I70</recordid><startdate>19991229</startdate><enddate>19991229</enddate><creator>ASKIN, DAVID</creator><creator>SAGER, JESS, W</creator><creator>ROSSEN, KAI</creator><creator>VOLANTE, RALPH, P., REIDER, PAUL, J</creator><scope>EVB</scope></search><sort><creationdate>19991229</creationdate><title>PROCESS FOR MAKING HIV PROTEASE INHIBITORS</title><author>ASKIN, DAVID ; SAGER, JESS, W ; ROSSEN, KAI ; VOLANTE, RALPH, P., REIDER, PAUL, J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_EA000637B13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; rus</language><creationdate>1999</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>ASKIN, DAVID</creatorcontrib><creatorcontrib>SAGER, JESS, W</creatorcontrib><creatorcontrib>ROSSEN, KAI</creatorcontrib><creatorcontrib>VOLANTE, RALPH, P., REIDER, PAUL, J</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>ASKIN, DAVID</au><au>SAGER, JESS, W</au><au>ROSSEN, KAI</au><au>VOLANTE, RALPH, P., REIDER, PAUL, J</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>PROCESS FOR MAKING HIV PROTEASE INHIBITORS</title><date>1999-12-29</date><risdate>1999</risdate><abstract>1. A process for forming a compound (I) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is C1-10 alkyl or aryl; comprising (a) reacting (A), (B), (C) and (D) to form a compound (F) wherein (A) is H2 N-(CH2)2-NHR where R is as defined above; (B) is selected from a halogenated acetaldehyde or a halogenated acetaldehyde C1-2 alkylacetal; (C) is R -CO2H where R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl; and (D) is R NC where R is as defined above; and (b) deblocking the compound (F) to form the compound (I) 2. A process for forming a compound (F) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; and R is selected from hydrogen, C1-10 alkyl, mono-, di- or tri-halogenated C1-10 alkyl or aryl and R is C1-10 alkyl or aryl wherein comprising reacting an imine (C) with R NC in the presence of a carboxylic acid, R - CO2H, to form the compound (F) 3. The process of Claim 2, wherein the imine (C) is formed by reacting an ethylene diamine compound A of the formula H2N-(CH2)2-NHR with a halogenated acetaldehyde or a halogenated acetaldehyde di-C1-2 alkylacetal. 4. The process of Claim 2, wherein the compound (F) is prepared in one-pot without first isolating the imine (C) 5. The process of Claim 2, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 6. The process of Claim 5, wherein R is and R is t-butyl. 7. A process for forming a compound (J) comprising the steps of: 1) reacting a nitrile (H) where R is a group of formula with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form a compound of formula 2) resolving the racemic compound to isolate a compound 1 3) reacting the compound 1 with a compound 2 to form a compound 3 4) deblocking the compound 3 to form a compound J 8. A process for forming an amide (G) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; comprising reacting a nitrile (H) with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form the amide (G) 9. The process of Claim 8, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 10. The process of Claim 11, wherein R is 11. The process of Claim 10, wherein the strong acid is selected from H2S04, H3P04, CH3S03H or BF3. 12. The process of Claim 8, wherein the strong acid is H2S04. 13. The process of Claim 8, wherein the nitrile (H) is prepared by reacting an imine (C) with a cyanide ion to form the nitrile (H). 14. The process of Claim 13, wherein the imine (C) is prepared by reacting an ethylene diamine compound (A) of the formula H2N(CH2)2 NHR with a halogenated acetaldehyde or a halogenated acetaldehyde di-C1-2 alkylacetal. 15. The process of Claim 16, wherein preparation of nitrile (H) ' is accomplished in one-pot without first isolating the imine (C). 16. A compound of the formula (C) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl where said substituent is aryl or heteroaryl. 17. The compound of Claim 16, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 18. The compound of Claim 17, wherein R is 19. A compound of the formula (H) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl where said substituent is aryl or heteroaryl. 20. The compound of Claim 19, wherein R is substituted C1-5 alkyl where said substituent is heteroaryl. 21. The compound of Claim 20, wherein R is 22. A process for forming an amide (G) wherein R is selected from hydrogen, C1-10 alkoxycarbonyl or unsubstituted or substituted C1-10 alkyl wherein said substitutent is aryl or heteroaryl; comprising (a) reacting a compound (A), H2N-(CH2)2-NHR where R is as defined above, a compound (B) selected from a halogenated acetaldehyde or a halogenated acetaldehyde C1-2 alkylacetal and a cyanide ion to form a nitrile (H) (b) reacting the nitrile (H) with a compound selected from t-butanol, isobutylene or t-butyl ester in the presence of a strong acid to form the amide (G) 23. A process for forming a compound (I) comprising the steps of: 1) reacting an imine (C) with R NC in the presence of carboxylic acid, R -CO2H to form a compound (F) where R is and R is t-butyl 2) deblocking the compound (F) to form the racemic compound (I) 3) resolving the racemic compound to isolate a compound 1 24. A process for forming a compound (J) comprising the steps of: 1) reacting imine (C) with R NC in the presence of carboxylic acid, R -CO2H to form the compound (F) where R is and R is t-butyl, 2) deblocking the compound (F) to form the racemic compound (I) 3) resolving the racemic compound to isolate a compound 1 4) reacting with compound 2 to form a compound 3 5) deblocking the compound 3 to form the compound (J).</abstract><edition>6</edition><oa>free_for_read</oa></addata></record> |
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| subjects | CHEMISTRY HETEROCYCLIC COMPOUNDS METALLURGY ORGANIC CHEMISTRY |
| title | PROCESS FOR MAKING HIV PROTEASE INHIBITORS |
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