Process for preparation of (-)3(S)-methylbenzoxazine derivative

Details Process for preparation of (-)3(S)-methylbenzoxazine derivative Process for preparation of (-)3(S)-methylbenzoxazine derivative

1996-03-11

1998-05-26

Ford, John M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C07D26536

Patent

active

057567310

ABSTRACT:
A process for preparing (-)3(S)-methylbenzoxazine derivative of formula (I) comprising the steps of reacting the compound of formula (II) with benzoic acid, triphenylphosphine and diethyl azodicarboxylate in an organic solvent to obtain the compound of formula (III); hydrogenating the compound of formula (III) in the presence of a metallic catalyst to provide the compound of formula (IV); hydrolyzing the compound of formula (IV) to give the compound of formula (V); and reacting the compound of formula (V) with diethyl azodicarboxylate, triphenylphosphine, and zinc chloride in an organic solvent. The obtained (-)3(S)-methylbenzoxazine derivative is a useful intermediate for preparing an antibacterial agent which has a potent bacteriocidal effect. ##STR1##

REFERENCES:
Hayakawa et al., "Synthesis and Antibacterial Activities of Substituted Chem. Pharm. Bull., 4907-4913 (1984).
Atarashi et al., "Synthesis and Antibacterial Activities of Optically Active Ofloxacin and Its Fluoromethyl Derivative," Chem. Pharm. Bull., 1896-1902 (1987).
Toshihiro et al., "Process for the Preparation of Benzoxazine Derivatives," Chem. Abstr., 111:134170z (1989).
Toshihiro et al., "Preparation of Resolution with N-(substituted sulfonyl-(R)-proline," Chem. Abstr. 112:35875x (Jul., 1989).
Hiroki et al., "Resolution of 112:198397g (Oct., 1989).
Hiroki et al., "Optical Separation of Abstr., 113:76637K (1990).

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