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Conversion of a racemic mixture of 8‐chloro‐2‐(2,6‐difluorophenylmethyl)‐2,3‐dihydro‐3‐methyl‐1,2,5‐benzothiadiazepin‐4(5h)‐one 1,1‐dioxide into a single enantiomer via a chromatographic resolution/racemization method
Author(s) -
La Torre F.,
Cirilli R.,
Ferretti R.,
Gallinella B.,
Costi R.,
Di Santo R.
Publication year - 2003
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.10226
Subject(s) - chemistry , racemization , enantiomer , chiral stationary phase , high performance liquid chromatography , enantiomeric excess , racemic mixture , chromatography , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
A simple and efficient strategy to convert the racemic mixture of 8‐chloro‐2‐(2,6‐difluorophenylmethyl)‐2,3‐dihydro‐3‐methyl‐1,2,5‐benzothiadiazepin‐4(5 H )‐one 1,1‐dioxide, a new anti‐HIV‐1 agent targeted to reverse transcriptase, into the more active ( S )‐enantiomer is described. The method utilizes repetition of the following two steps: 1) semipreparative enantioseparation by HPLC on chiral stationary phase; 2) base‐induced racemization of the less active ( R )‐enantiomer. Chirality 15:429–432, 2003. © 2003 Wiley‐Liss, Inc.