A chemoselective, acid mediated conversion of amide acetal to oxazole: The key step in the synthesis of cardiovascular drug, ifetroban sodium

Shankar Swaminathan; Ambarish K. Singh; Wen Sen Li; John J. Venit; Kenneth J. Natalie; James H. Simpson; Raymond E. Weaver; Lee J. Silverberg

doi:10.1016/S0040-4039(98)00904-6

A chemoselective, acid mediated conversion of amide acetal to oxazole: The key step in the synthesis of cardiovascular drug, ifetroban sodium

Shankar Swaminathan, Ambarish K. Singh, Wen Sen Li, John J. Venit, Kenneth J. Natalie, James H. Simpson, Raymond E. Weaver, Lee J. Silverberg

Penn State Schuylkill

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

The cyclization of acetal amide was carried out with trimethylsilyl trifluoromethanesulfonate, followed by elimination using sodium methoxide to give 2,5-disubstituted oxazole, thus completing a new route to the cardiovascular drug ifetroban sodium.

Original language	English (US)
Pages (from-to)	4769-4772
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4039(98)00904-6
State	Published - Jul 2 1998

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(98)00904-6

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abstract = "The cyclization of acetal amide was carried out with trimethylsilyl trifluoromethanesulfonate, followed by elimination using sodium methoxide to give 2,5-disubstituted oxazole, thus completing a new route to the cardiovascular drug ifetroban sodium.",

author = "Shankar Swaminathan and Singh, {Ambarish K.} and Li, {Wen Sen} and Venit, {John J.} and Natalie, {Kenneth J.} and Simpson, {James H.} and Weaver, {Raymond E.} and Silverberg, {Lee J.}",

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AU - Li, Wen Sen

AU - Venit, John J.

AU - Natalie, Kenneth J.

AU - Simpson, James H.

AU - Weaver, Raymond E.

AU - Silverberg, Lee J.

PY - 1998/7/2

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AB - The cyclization of acetal amide was carried out with trimethylsilyl trifluoromethanesulfonate, followed by elimination using sodium methoxide to give 2,5-disubstituted oxazole, thus completing a new route to the cardiovascular drug ifetroban sodium.

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A chemoselective, acid mediated conversion of amide acetal to oxazole: The key step in the synthesis of cardiovascular drug, ifetroban sodium

Abstract

All Science Journal Classification (ASJC) codes

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