Phenylserine amides and the preparation of phenylserines/phenyls

Details Phenylserine amides and the preparation of phenylserines/phenyls Phenylserine amides and the preparation of phenylserines/phenyls

1996-06-12

1998-06-30

Achutamurthy, Ponnathapura

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435116, 435136, 435170, 435227, 435228, 562444, 562401, 562445, 562567, 562570, C12P 1306, C12P 740, C12N 978, C07B 5500

Patent

active

057732841

ABSTRACT:
Process for the preparation of a threo-phenylserine amide of the general formula 2 in which glycine amide is contacted with the corresponding substituted benzaldehyde of formula 3 in an excess relative to the amount of glycine amide, this taking place at a pH between 9 and 14 in the presence of a suitable solvent. The resulting phenylserine amide can subsequently be hydrolyzed to a phenylserine amide of the general formula 1, which is subsequently hydrolyzed to a phenylserine amide of the general formula 1, which is subsequently subjected to a stereoselective enzymatic hydrolysis yielding a (2S,3R) phenylserine. The non-hydrolyzed (2R,3S) phenylserine amide can be isolated as a Schiff base and be recirculated and simply racemized. The (2S,3R) phenylserine obtained can be used in the preparation of thiamphenicol or florfenicol. The threo-phenylserine amides of the general formula 1 or 2 are new intermediates in this commercially attractive process for the preparation of thiamphenicol and florfenicol.

REFERENCES:
patent: 3971700 (1976-07-01), Boesten
patent: 4501919 (1985-02-01), Koch et al.
patent: 5215897 (1993-06-01), Sakashita et al.
patent: 5248608 (1993-09-01), Van Dooren et al.

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