PROCESS FOR THE PRODUCTION OF (+) BIOTIN
Process for the production of (+) biotin. A compound of the formula: wherein R1 is e.g., an (R)-1-phenylalkyl group, and R2 is, e.g., hydrogen. The desired diastereomer of the formula: is separated out. If R2 is H, a protective group is introduced by reaction with, e.g., an aliphatic acid chloride....
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| creator | MCGARRITY JOHN TENUD LEANDER |
| description | Process for the production of (+) biotin. A compound of the formula: wherein R1 is e.g., an (R)-1-phenylalkyl group, and R2 is, e.g., hydrogen. The desired diastereomer of the formula: is separated out. If R2 is H, a protective group is introduced by reaction with, e.g., an aliphatic acid chloride. The diastereomer is converted by reaction with a thiocarboxylic acid salt derivative into the corresponding thiolacetone, which is reacted with a Grignard reactant and subsequently water is split off. Alternatively, the corresponding thiolacetone is reacted with a compound of the formula: (C6H5)3P(+)(CH2)4COOR3.X(-) wherein R3 is, e.g., H, and X is a halogen atom, in the presence of a base to provide a compound of the formula: Such compound is catalytically hydrogenated and then converted into (+) biotin by cleavage of the protective groups. |
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If R2 is H, a protective group is introduced by reaction with, e.g., an aliphatic acid chloride. The diastereomer is converted by reaction with a thiocarboxylic acid salt derivative into the corresponding thiolacetone, which is reacted with a Grignard reactant and subsequently water is split off. Alternatively, the corresponding thiolacetone is reacted with a compound of the formula: (C6H5)3P(+)(CH2)4COOR3.X(-) wherein R3 is, e.g., H, and X is a halogen atom, in the presence of a base to provide a compound of the formula: Such compound is catalytically hydrogenated and then converted into (+) biotin by cleavage of the protective groups.</description><language>eng</language><subject>APPARATUS THEREFOR ; CHEMISTRY ; GENERAL METHODS OF ORGANIC CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>1992</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=19920526&DB=EPODOC&CC=US&NR=5117003A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76289</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19920526&DB=EPODOC&CC=US&NR=5117003A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>MCGARRITY; JOHN</creatorcontrib><creatorcontrib>TENUD; LEANDER</creatorcontrib><title>PROCESS FOR THE PRODUCTION OF (+) BIOTIN</title><description>Process for the production of (+) biotin. 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A compound of the formula: wherein R1 is e.g., an (R)-1-phenylalkyl group, and R2 is, e.g., hydrogen. The desired diastereomer of the formula: is separated out. If R2 is H, a protective group is introduced by reaction with, e.g., an aliphatic acid chloride. The diastereomer is converted by reaction with a thiocarboxylic acid salt derivative into the corresponding thiolacetone, which is reacted with a Grignard reactant and subsequently water is split off. Alternatively, the corresponding thiolacetone is reacted with a compound of the formula: (C6H5)3P(+)(CH2)4COOR3.X(-) wherein R3 is, e.g., H, and X is a halogen atom, in the presence of a base to provide a compound of the formula: Such compound is catalytically hydrogenated and then converted into (+) biotin by cleavage of the protective groups.</abstract><oa>free_for_read</oa></addata></record> |
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| subjects | APPARATUS THEREFOR CHEMISTRY GENERAL METHODS OF ORGANIC CHEMISTRY HETEROCYCLIC COMPOUNDS METALLURGY ORGANIC CHEMISTRY |
| title | PROCESS FOR THE PRODUCTION OF (+) BIOTIN |
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