An asymmetric synthesis of 3-aryl-1,4-oxazin-2-ones: Synthesis of a key intermediate of an NK1 receptor antagonist

Paul N. Devine; Bruce S. Foster; Edward J.J. Grabowski; Paul J. Reider

doi:10.3987/com-02-s(m)54

An asymmetric synthesis of 3-aryl-1,4-oxazin-2-ones: Synthesis of a key intermediate of an NK₁ receptor antagonist

Paul N. Devine
, Bruce S. Foster
, Edward J.J. Grabowski
, Paul J. Reider

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

13 Scopus citations

Abstract

Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly diastereoselective coupling reaction between racemic α-halo acids and N-benzylethanolamine. The adducts are readily cyclized upon treatment with a catalytic amount of TsOH giving the above titled compounds in >90% ee. The 4-fluorophenyl substituted oxazinone thus formed is the key intermediate in the synthesis of a potent NK₁ receptor antagonist.

Original language	English (US)
Pages (from-to)	119-123
Number of pages	5
Journal	Heterocycles
Volume	58
DOIs	https://doi.org/10.3987/com-02-s(m)54
State	Published - Nov 22 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly diastereoselective coupling reaction between racemic α-halo acids and N-benzylethanolamine. The adducts are readily cyclized upon treatment with a catalytic amount of TsOH giving the above titled compounds in >90\% ee. The 4-fluorophenyl substituted oxazinone thus formed is the key intermediate in the synthesis of a potent NK1 receptor antagonist.",

author = "Devine, \{Paul N.\} and Foster, \{Bruce S.\} and Grabowski, \{Edward J.J.\} and Reider, \{Paul J.\}",

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doi = "10.3987/com-02-s(m)54",

language = "English (US)",

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journal = "Heterocycles",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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T2 - Synthesis of a key intermediate of an NK1 receptor antagonist

AU - Devine, Paul N.

AU - Foster, Bruce S.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

PY - 2002/11/22

Y1 - 2002/11/22

N2 - Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly diastereoselective coupling reaction between racemic α-halo acids and N-benzylethanolamine. The adducts are readily cyclized upon treatment with a catalytic amount of TsOH giving the above titled compounds in >90% ee. The 4-fluorophenyl substituted oxazinone thus formed is the key intermediate in the synthesis of a potent NK1 receptor antagonist.

AB - Pyrrolidine derived (S)-lactamide auxiliaries mediate a highly diastereoselective coupling reaction between racemic α-halo acids and N-benzylethanolamine. The adducts are readily cyclized upon treatment with a catalytic amount of TsOH giving the above titled compounds in >90% ee. The 4-fluorophenyl substituted oxazinone thus formed is the key intermediate in the synthesis of a potent NK1 receptor antagonist.

UR - https://www.scopus.com/pages/publications/0037159786

UR - https://www.scopus.com/pages/publications/0037159786#tab=citedBy

U2 - 10.3987/com-02-s(m)54

DO - 10.3987/com-02-s(m)54

M3 - Article

AN - SCOPUS:0037159786

SN - 0385-5414

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SP - 119

EP - 123

JO - Heterocycles

JF - Heterocycles

ER -

An asymmetric synthesis of 3-aryl-1,4-oxazin-2-ones: Synthesis of a key intermediate of an NK₁ receptor antagonist

Abstract

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