First synthesis of the two enantiomers of α‐methyldiphenylalanine [(αMe)Dip] by HPLC resolution | Zendy

Royo Soledad | Zendy; López Pilar | Zendy; Jiménez Ana I. | Zendy; Oliveros Laureano | Zendy; Cativiela Carlos | Zendy

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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.

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