Process for S-metoprolol via oxazolidin-2-one

Details Process for S-metoprolol via oxazolidin-2-one Process for S-metoprolol via oxazolidin-2-one

1990-05-30

1991-07-23

Daus, Donald G.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

564348, 560205, C07D23302

Patent

active

050345354

ABSTRACT:
A process for preparing S-metoprolol of the formula ##STR1## or a salt thereof, with high enantiomeric purity, is described, whereby a (S)-5-hydroxymethyl-3-isopropyloxazolidin-2-one sulfonic acid ester of the formula ##STR2## is prepared, and further reacted with 4-[2-methoxyethyl]phenol of the formula ##STR3## and the resulting intermediate of the formula ##STR4## is hydrolysed to S-metoprolol, and whereby the (S)-5-hydroxymethyl-3-isopropyloxazolidin-2-one sulfonic acid ester of formula II is prepared by reacting (S)-3-isopropylamino-1,2-propanediol of the formula ##STR5## with a chloroformic acid ester of the formula ##STR6## wherein R' is an alkyl group having 1-3 carbon atoms or a phenyl group, to the formation of (S)-5-hydroxymethyl-3-isopropyloxazolidin-2-one of the formula ##STR7## which is reacted with an activated sulfonic acid of the formula ##STR8## wherein R" is an aryl group such as tolyl and X is a halogen such as Cl, to formation of the ester of formula II, which when required is enriched with the (S)-enantiomer by crystallization.

REFERENCES:
patent: 3641152 (1972-02-01), Shavel
patent: 3930016 (1975-12-01), Berntsson et al.
patent: 4287351 (1981-09-01), Bourgery et al.
patent: 4296242 (1981-10-01), Nagabhushan
Chem. Abst. vol. 105, Entry 152694d (1986).
Chemical Abstracts, vol. 100, No. 21 21st May 1984 p. 598, No. 174473e. Columbus, Ohio, US; Maruko Pharmaceutical Co. Ltd.

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