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

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

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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T2 - The key step in the synthesis of cardiovascular drug, ifetroban sodium

AU - Swaminathan, Shankar

AU - Singh, Ambarish K.

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

Y1 - 1998/7/2

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/0032474717

UR - https://www.scopus.com/pages/publications/0032474717#tab=citedBy

U2 - 10.1016/S0040-4039(98)00904-6

DO - 10.1016/S0040-4039(98)00904-6

M3 - Article

AN - SCOPUS:0032474717

SN - 0040-4039

VL - 39

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EP - 4772

JO - Tetrahedron Letters

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IS - 27

ER -

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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