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First synthesis of the two enantiomers of α‐methyldiphenylalanine [(αMe)Dip] by HPLC resolution
Author(s) -
Royo Soledad,
López Pilar,
Jiménez Ana I.,
Oliveros Laureano,
Cativiela Carlos
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10036
Subject(s) - chemistry , enantiomer , high performance liquid chromatography , acetone , chromatography , chiral stationary phase , resolution (logic) , yield (engineering) , chiral column chromatography , hexane , cellulose , chiral resolution , phase (matter) , covalent bond , organic chemistry , materials science , artificial intelligence , computer science , metallurgy
A strategy for the preparation of enantiomerically pure (R)‐ and (S)‐α‐methyldiphenylalanine, constrained phenylalanine analogs, is described. A racemic precursor was prepared in high yield from easily available starting products and subjected to HPLC resolution on a noncommercial chiral stationary phase. More than 600 mg of each enantiomer was isolated in optically pure form by using a 150 × 20 mm ID column containing mixed 10‐undecenoate/3,5‐dimethylphenylcarbamate of cellulose covalently bonded to allylsilica gel and a mixture of n ‐hexane/2‐propanol/acetone as the mobile phase. Chirality 14:39–46, 2002. © 2002 Wiley‐Liss, Inc.