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Title 

Facile ring opening reaction of oxazolone enables efficient amidation for aminoisobutyric acid

 

아미노부틸산의 효율적인 아마이드화를 가능케하는 옥사졸론의 facile 고리 열기 반응

Authors 

M JoS W WonD G LeeJ YunSunhong KimY S Kwak

Publisher 

Pharmaceutical Society of Korea

Issue Date 

2018

Citation 

Archives of Pharmacal Research

Keywords 

4,4-DimethyloxazoloneAmidationAminoisobutyric acid (AIB)Urea by-product

Abstract 

Abstract: 4,4-Dimethyloxazolones derived from N-protected aminoisobutyric acid (AIB) are particularly known as poor electrophiles due to the steric hindrance around the carbonyl and not employed as useful intermediates for amidation whereas numerous examples have been reported to support the utility of other oxazolones in amidation. AIB is an important and strategical synthon in medicinal chemistry but the peptide bond formation of the N-protected urethane derivatives of AIB is known to be often unproductive due to the rapid formation of the stable 4,4-dimethyloxazolone via an intramolecular cyclization. We discovered that the 4,4-dimethyloxazolone of an AIB urethane is in fact an excellent electrophile that enables efficient amidation even with weakly reactive nucleophiles. The 4,4-dimethyloxazolone can be stored in a pure form and used as a reagent offering an efficient and convenient synthetic tool for generating AIB-peptide analogs

ISSN 

0253-6269

Link 

http://dx.doi.org/10.1007/s12272-018-1031-5

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


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