Loading…
An Asymmetric Synthesis of Clopidogrel Hydrogen Sulfate
Abstract An asymmetric synthesis of ( S )-(+)-clopidogrel hydrogen sulfate has been developed through application of a Strecker reaction with [(1 S )-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of 2-chlorobenzaldehyde to a solution of sodium cyanide and [(1 S )-1-(4-...
Saved in:
| Published in: | Synthesis (Stuttgart) 2013-03, Vol.45 (5), p.621-624 |
|---|---|
| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
| Citations: | Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c277t-2f360f0e86dfd900fce13764a570ec74afd31f7f6cad211a9f550b45c7525eab3 |
|---|---|
| cites | |
| container_end_page | 624 |
| container_issue | 5 |
| container_start_page | 621 |
| container_title | Synthesis (Stuttgart) |
| container_volume | 45 |
| creator | Sashikanth, Suthrapu Raju, Veeramalla Somaiah, Sripathi Rao, Peddi Srinivasa Reddy, Karnati Venugopal |
| description | Abstract
An asymmetric synthesis of (
S
)-(+)-clopidogrel hydrogen sulfate has been developed through application of a Strecker reaction with [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of 2-chlorobenzaldehyde to a solution of sodium cyanide and [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride gave diastereoisomerically pure (2
S
)-(2-chlorophenyl){[(1
S
)-1-(4-methoxyphenyl)ethyl]amino}acetonitrile hydrochloride. Cleavage of the chiral auxiliary and concomitant hydrolysis of the nitrile group then gave enantiomerically pure (2
S
)-2-(2-chlorophenyl)glycine hydrochloride, a key intermediate for (
S
)-(+)-clopidogrel. |
| doi_str_mv | 10.1055/s-0032-1316852 |
| format | article |
| fullrecord | <record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_0032_1316852</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_0032_1316852</sourcerecordid><originalsourceid>FETCH-LOGICAL-c277t-2f360f0e86dfd900fce13764a570ec74afd31f7f6cad211a9f550b45c7525eab3</originalsourceid><addsrcrecordid>eNp1jztPwzAUhS0EEqGwMucPuFzbcZyMUQQUqRJDQWKzXPu6TZVHZadD_j2p2rXTGc5D5yPklcGSgZRvkQIITplgeSH5HUlYJhTlDP7uSTJbJVVFwR7JU4wHAFBclAlRVZ9Wceo6HENj083Uj3uMTUwHn9btcGzcsAvYpqvJhWGHfbo5td6M-EwevGkjvlx1QX4_3n_qFV1_f37V1ZpartRIuRc5eMAid96VAN4iEyrPjFSAVmXGO8G88rk1jjNmSi8lbDNpleQSzVYsyPKya8MQY0Cvj6HpTJg0A33G1lGfsfUVey7QS2HcN9ihPgyn0M8Pb-X_AU3zWMs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>An Asymmetric Synthesis of Clopidogrel Hydrogen Sulfate</title><source>Thieme Connect Journals</source><creator>Sashikanth, Suthrapu ; Raju, Veeramalla ; Somaiah, Sripathi ; Rao, Peddi Srinivasa ; Reddy, Karnati Venugopal</creator><creatorcontrib>Sashikanth, Suthrapu ; Raju, Veeramalla ; Somaiah, Sripathi ; Rao, Peddi Srinivasa ; Reddy, Karnati Venugopal</creatorcontrib><description>Abstract
An asymmetric synthesis of (
S
)-(+)-clopidogrel hydrogen sulfate has been developed through application of a Strecker reaction with [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of 2-chlorobenzaldehyde to a solution of sodium cyanide and [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride gave diastereoisomerically pure (2
S
)-(2-chlorophenyl){[(1
S
)-1-(4-methoxyphenyl)ethyl]amino}acetonitrile hydrochloride. Cleavage of the chiral auxiliary and concomitant hydrolysis of the nitrile group then gave enantiomerically pure (2
S
)-2-(2-chlorophenyl)glycine hydrochloride, a key intermediate for (
S
)-(+)-clopidogrel.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0032-1316852</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2013-03, Vol.45 (5), p.621-624</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c277t-2f360f0e86dfd900fce13764a570ec74afd31f7f6cad211a9f550b45c7525eab3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0032-1316852.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0032-1316852$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Sashikanth, Suthrapu</creatorcontrib><creatorcontrib>Raju, Veeramalla</creatorcontrib><creatorcontrib>Somaiah, Sripathi</creatorcontrib><creatorcontrib>Rao, Peddi Srinivasa</creatorcontrib><creatorcontrib>Reddy, Karnati Venugopal</creatorcontrib><title>An Asymmetric Synthesis of Clopidogrel Hydrogen Sulfate</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
An asymmetric synthesis of (
S
)-(+)-clopidogrel hydrogen sulfate has been developed through application of a Strecker reaction with [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of 2-chlorobenzaldehyde to a solution of sodium cyanide and [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride gave diastereoisomerically pure (2
S
)-(2-chlorophenyl){[(1
S
)-1-(4-methoxyphenyl)ethyl]amino}acetonitrile hydrochloride. Cleavage of the chiral auxiliary and concomitant hydrolysis of the nitrile group then gave enantiomerically pure (2
S
)-2-(2-chlorophenyl)glycine hydrochloride, a key intermediate for (
S
)-(+)-clopidogrel.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp1jztPwzAUhS0EEqGwMucPuFzbcZyMUQQUqRJDQWKzXPu6TZVHZadD_j2p2rXTGc5D5yPklcGSgZRvkQIITplgeSH5HUlYJhTlDP7uSTJbJVVFwR7JU4wHAFBclAlRVZ9Wceo6HENj083Uj3uMTUwHn9btcGzcsAvYpqvJhWGHfbo5td6M-EwevGkjvlx1QX4_3n_qFV1_f37V1ZpartRIuRc5eMAid96VAN4iEyrPjFSAVmXGO8G88rk1jjNmSi8lbDNpleQSzVYsyPKya8MQY0Cvj6HpTJg0A33G1lGfsfUVey7QS2HcN9ihPgyn0M8Pb-X_AU3zWMs</recordid><startdate>20130301</startdate><enddate>20130301</enddate><creator>Sashikanth, Suthrapu</creator><creator>Raju, Veeramalla</creator><creator>Somaiah, Sripathi</creator><creator>Rao, Peddi Srinivasa</creator><creator>Reddy, Karnati Venugopal</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130301</creationdate><title>An Asymmetric Synthesis of Clopidogrel Hydrogen Sulfate</title><author>Sashikanth, Suthrapu ; Raju, Veeramalla ; Somaiah, Sripathi ; Rao, Peddi Srinivasa ; Reddy, Karnati Venugopal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c277t-2f360f0e86dfd900fce13764a570ec74afd31f7f6cad211a9f550b45c7525eab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sashikanth, Suthrapu</creatorcontrib><creatorcontrib>Raju, Veeramalla</creatorcontrib><creatorcontrib>Somaiah, Sripathi</creatorcontrib><creatorcontrib>Rao, Peddi Srinivasa</creatorcontrib><creatorcontrib>Reddy, Karnati Venugopal</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sashikanth, Suthrapu</au><au>Raju, Veeramalla</au><au>Somaiah, Sripathi</au><au>Rao, Peddi Srinivasa</au><au>Reddy, Karnati Venugopal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Asymmetric Synthesis of Clopidogrel Hydrogen Sulfate</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2013-03-01</date><risdate>2013</risdate><volume>45</volume><issue>5</issue><spage>621</spage><epage>624</epage><pages>621-624</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
An asymmetric synthesis of (
S
)-(+)-clopidogrel hydrogen sulfate has been developed through application of a Strecker reaction with [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride as a chiral auxiliary. Addition of 2-chlorobenzaldehyde to a solution of sodium cyanide and [(1
S
)-1-(4-methoxyphenyl)ethyl]amine hydrochloride gave diastereoisomerically pure (2
S
)-(2-chlorophenyl){[(1
S
)-1-(4-methoxyphenyl)ethyl]amino}acetonitrile hydrochloride. Cleavage of the chiral auxiliary and concomitant hydrolysis of the nitrile group then gave enantiomerically pure (2
S
)-2-(2-chlorophenyl)glycine hydrochloride, a key intermediate for (
S
)-(+)-clopidogrel.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0032-1316852</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0039-7881 |
| ispartof | Synthesis (Stuttgart), 2013-03, Vol.45 (5), p.621-624 |
| issn | 0039-7881 1437-210X |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_0032_1316852 |
| source | Thieme Connect Journals |
| title | An Asymmetric Synthesis of Clopidogrel Hydrogen Sulfate |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T21%3A11%3A14IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-thieme_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20Asymmetric%20Synthesis%20of%20Clopidogrel%20Hydrogen%20Sulfate&rft.jtitle=Synthesis%20(Stuttgart)&rft.au=Sashikanth,%20Suthrapu&rft.date=2013-03-01&rft.volume=45&rft.issue=5&rft.spage=621&rft.epage=624&rft.pages=621-624&rft.issn=0039-7881&rft.eissn=1437-210X&rft_id=info:doi/10.1055/s-0032-1316852&rft_dat=%3Cthieme_cross%3E10_1055_s_0032_1316852%3C/thieme_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c277t-2f360f0e86dfd900fce13764a570ec74afd31f7f6cad211a9f550b45c7525eab3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |