Unprecedented crystallization and X-ray crystal structure of racemic N(alpha)-(t-butyloxycarbonyl)-L-L-phenylalanine N-methoxy-N-methylamide.

Abstract:

:Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupling agent used. Single crystal X-ray analysis of the solid revealed that it is a racemate. The molecular packing of the crystals reflect the stability of the racemate as opposed to an enantiomerically pure solid.

journal_name

Chirality

journal_title

Chirality

authors

Zheng X,Donkor IO,Miller DD,Ross CR 2nd

doi

10.1002/(SICI)1520-636X(2000)12:1<2::AID-CHIR2>3.0

subject

Has Abstract

pub_date

2000-01-01 00:00:00

pages

2-6

issue

1

eissn

0899-0042

issn

1520-636X

pii

10.1002/(SICI)1520-636X(2000)12:1<2::AID-CHIR2>3.0

journal_volume

12

pub_type

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