Large-Scale Practical Synthesis of Boc-Protected 4‑Fluoro‑l‑Proline

Large-Scale Practical Synthesis of Boc-Protected 4‑Fluoro‑l‑Proline

A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-friendly and large-scale feasible process using a single solvent was developed to afford moderate yields o...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic process research & development 2020-09, Vol.24 (9), p.1609-1613
Hauptverfasser: Tamboli, Yasinalli, Kashid, Bharat, Yadav, Ram Prasad, Rafeeq, Mohammad, Merwade, Arvind Y
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1613
container_issue 9
container_start_page 1609
container_title Organic process research & development
container_volume 24
creator Tamboli, Yasinalli
Kashid, Bharat
Yadav, Ram Prasad
Rafeeq, Mohammad
Merwade, Arvind Y
description A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-friendly and large-scale feasible process using a single solvent was developed to afford moderate yields of products with excellent purity >99% by high-performance liquid chromatography . The key feature of the optimization involving chromatography-free purification and isolation on a kilogram-scale at a pilot plant scale is described.
doi_str_mv 10.1021/acs.oprd.0c00080
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acs_oprd_0c00080</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>a951996397</sourcerecordid><originalsourceid>FETCH-LOGICAL-a280t-1cfca55de8b9b51bb7bbb72a0de72843358fd7e85fdd9c3a56f086852aaef9b3</originalsourceid><addsrcrecordid>eNp1kE1OwzAQhS0EEqWwZ5kD4DB2asdZQkVLpUhUahfsIv9CqhBXdrrojitwRU6Co3bLYjRPeu-NRh9C9wRyApQ8Sh1zvw8mBw0AAi7QhDAKmAn-fpk0iAJzwuEa3cS4SxHGCZ2gVS3Dh8UbLTubrYPUQ5tktjn2w6eNbcy8y569xuvgB6sHa7LZ7_fPojv44JPo0iSra3t7i66c7KK9O-8p2i5etvNXXL8tV_OnGksqYMBEOy0ZM1aoSjGiVKnSUAnGllTMioIJZ0ormDOm0oVk3IHgglEpratUMUVwOquDjzFY1-xD-yXDsSHQjCSaRKIZSTRnEqnycKqMzs4fQp_--z_-B9kfZjs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Large-Scale Practical Synthesis of Boc-Protected 4‑Fluoro‑l‑Proline</title><source>ACS Publications</source><creator>Tamboli, Yasinalli ; Kashid, Bharat ; Yadav, Ram Prasad ; Rafeeq, Mohammad ; Merwade, Arvind Y</creator><creatorcontrib>Tamboli, Yasinalli ; Kashid, Bharat ; Yadav, Ram Prasad ; Rafeeq, Mohammad ; Merwade, Arvind Y</creatorcontrib><description>A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-friendly and large-scale feasible process using a single solvent was developed to afford moderate yields of products with excellent purity &gt;99% by high-performance liquid chromatography . The key feature of the optimization involving chromatography-free purification and isolation on a kilogram-scale at a pilot plant scale is described.</description><identifier>ISSN: 1083-6160</identifier><identifier>EISSN: 1520-586X</identifier><identifier>DOI: 10.1021/acs.oprd.0c00080</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organic process research &amp; development, 2020-09, Vol.24 (9), p.1609-1613</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a280t-1cfca55de8b9b51bb7bbb72a0de72843358fd7e85fdd9c3a56f086852aaef9b3</citedby><cites>FETCH-LOGICAL-a280t-1cfca55de8b9b51bb7bbb72a0de72843358fd7e85fdd9c3a56f086852aaef9b3</cites><orcidid>0000-0002-2816-765X ; 0000-0002-5161-0170</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.oprd.0c00080$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.oprd.0c00080$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids></links><search><creatorcontrib>Tamboli, Yasinalli</creatorcontrib><creatorcontrib>Kashid, Bharat</creatorcontrib><creatorcontrib>Yadav, Ram Prasad</creatorcontrib><creatorcontrib>Rafeeq, Mohammad</creatorcontrib><creatorcontrib>Merwade, Arvind Y</creatorcontrib><title>Large-Scale Practical Synthesis of Boc-Protected 4‑Fluoro‑l‑Proline</title><title>Organic process research &amp; development</title><addtitle>Org. Process Res. Dev</addtitle><description>A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-friendly and large-scale feasible process using a single solvent was developed to afford moderate yields of products with excellent purity &gt;99% by high-performance liquid chromatography . The key feature of the optimization involving chromatography-free purification and isolation on a kilogram-scale at a pilot plant scale is described.</description><issn>1083-6160</issn><issn>1520-586X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kE1OwzAQhS0EEqWwZ5kD4DB2asdZQkVLpUhUahfsIv9CqhBXdrrojitwRU6Co3bLYjRPeu-NRh9C9wRyApQ8Sh1zvw8mBw0AAi7QhDAKmAn-fpk0iAJzwuEa3cS4SxHGCZ2gVS3Dh8UbLTubrYPUQ5tktjn2w6eNbcy8y569xuvgB6sHa7LZ7_fPojv44JPo0iSra3t7i66c7KK9O-8p2i5etvNXXL8tV_OnGksqYMBEOy0ZM1aoSjGiVKnSUAnGllTMioIJZ0ormDOm0oVk3IHgglEpratUMUVwOquDjzFY1-xD-yXDsSHQjCSaRKIZSTRnEqnycKqMzs4fQp_--z_-B9kfZjs</recordid><startdate>20200918</startdate><enddate>20200918</enddate><creator>Tamboli, Yasinalli</creator><creator>Kashid, Bharat</creator><creator>Yadav, Ram Prasad</creator><creator>Rafeeq, Mohammad</creator><creator>Merwade, Arvind Y</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2816-765X</orcidid><orcidid>https://orcid.org/0000-0002-5161-0170</orcidid></search><sort><creationdate>20200918</creationdate><title>Large-Scale Practical Synthesis of Boc-Protected 4‑Fluoro‑l‑Proline</title><author>Tamboli, Yasinalli ; Kashid, Bharat ; Yadav, Ram Prasad ; Rafeeq, Mohammad ; Merwade, Arvind Y</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a280t-1cfca55de8b9b51bb7bbb72a0de72843358fd7e85fdd9c3a56f086852aaef9b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tamboli, Yasinalli</creatorcontrib><creatorcontrib>Kashid, Bharat</creatorcontrib><creatorcontrib>Yadav, Ram Prasad</creatorcontrib><creatorcontrib>Rafeeq, Mohammad</creatorcontrib><creatorcontrib>Merwade, Arvind Y</creatorcontrib><collection>CrossRef</collection><jtitle>Organic process research &amp; development</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tamboli, Yasinalli</au><au>Kashid, Bharat</au><au>Yadav, Ram Prasad</au><au>Rafeeq, Mohammad</au><au>Merwade, Arvind Y</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Large-Scale Practical Synthesis of Boc-Protected 4‑Fluoro‑l‑Proline</atitle><jtitle>Organic process research &amp; development</jtitle><addtitle>Org. Process Res. Dev</addtitle><date>2020-09-18</date><risdate>2020</risdate><volume>24</volume><issue>9</issue><spage>1609</spage><epage>1613</epage><pages>1609-1613</pages><issn>1083-6160</issn><eissn>1520-586X</eissn><abstract>A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-friendly and large-scale feasible process using a single solvent was developed to afford moderate yields of products with excellent purity &gt;99% by high-performance liquid chromatography . The key feature of the optimization involving chromatography-free purification and isolation on a kilogram-scale at a pilot plant scale is described.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.oprd.0c00080</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-2816-765X</orcidid><orcidid>https://orcid.org/0000-0002-5161-0170</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1083-6160
ispartof Organic process research & development, 2020-09, Vol.24 (9), p.1609-1613
issn 1083-6160
1520-586X
language eng
recordid cdi_crossref_primary_10_1021_acs_oprd_0c00080
source ACS Publications
title Large-Scale Practical Synthesis of Boc-Protected 4‑Fluoro‑l‑Proline
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-13T23%3A11%3A30IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Large-Scale%20Practical%20Synthesis%20of%20Boc-Protected%204%E2%80%91Fluoro%E2%80%91l%E2%80%91Proline&rft.jtitle=Organic%20process%20research%20&%20development&rft.au=Tamboli,%20Yasinalli&rft.date=2020-09-18&rft.volume=24&rft.issue=9&rft.spage=1609&rft.epage=1613&rft.pages=1609-1613&rft.issn=1083-6160&rft.eissn=1520-586X&rft_id=info:doi/10.1021/acs.oprd.0c00080&rft_dat=%3Cacs_cross%3Ea951996397%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true