Optical resolution of racemic mixtures of alpha-naphthylpropioni

Details Optical resolution of racemic mixtures of alpha-naphthylpropioni Optical resolution of racemic mixtures of alpha-naphthylpropioni

1986-03-27

1988-02-09

Mars, Howard T.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2605011, 562402, 562444, 562466, C07C 8730, C07B 5700

Patent

active

047241020

ABSTRACT:
A new process for the optical resolution of racemic mixtures of .alpha.-naphthylpropionic acids of formula ##STR1## wherein R.sub.1 is (C.sub.1-6) alkyl and R.sub.2 represents hydrogen or a halogen atom comprises reacting a racemic mixture of a compound of formula II ##STR2## wherein R.sub.1 and R.sub.2 have the above seen meanings and R.sub.3 is a reactive group, with an optically active aminoacid of formula ##STR3## wherein R.sub.4 represents a (C.sub.1-8) alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl or carboxy, and m is an integer from 0 to 4, to give a pair of diastereoisomeric amides of formula ##STR4## wherein R.sub.1, R.sub.2, R.sub.4 and m have the above seen meanings, and M is a hydrogen atom or a cation of an alkali metal or a cation of an organic base. Compounds IV are resolved into the single diastereoisomeric amides d,d or 1,d, or d,1 or 1,1. Acid hydrolysis gives the optically active compound I.

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patent: 3904683 (1975-09-01), Day et al.
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patent: 4246164 (1981-01-01), Felder et al.
patent: 4246193 (1981-01-01), Holton
patent: 4399284 (1983-08-01), Cannata et al.

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