Intermediates in a resolution process for racemic spiro hydantoi

Details Intermediates in a resolution process for racemic spiro hydantoi Intermediates in a resolution process for racemic spiro hydantoi

1990-06-25

1991-04-09

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 15, 548308, 548309, C07D21538, C07D49110

Patent

active

050066579

ABSTRACT:
A novel three-step process for resolving a racemic spiro-hydantoin compound into its optical antipodes is disclosed, which involves (1) reacting said racemic compound with an optically-active asymmetric isocyanate of the formula RNCO, wherein R is (S)- or (R)-1-phenylethyl or (S)-or (R)-1-(1-naphthyl)ethyl, to form the corresponding diastereomeric ureido compound; (2) separating the resulting diastereomeric mixture into its component parts, and (3) thereafter converting the separated ureido diasteromers obtained in step (b) to the corresponding asymmetric hydantoin compounds by treatment with an alkali metal lower alkoxide (C.sub.1 -C.sub.4), followed by acidification, whereupon the desired optical isomer is obtained. The final products so obtained, such as (4S)-(+)-6-fluoro-2,3-dihydro-spiro-[4H-1-benzopyran-4,4'-imidazolidine]-2 ',5'-dione(sorbinil) and (5'S)-3'-chloro-5', 6',7',8'-tetrahydro-spiro[imidazolidine-4,5'-quinoline]-2,5-dione, are known to be useful in preventing or alleviating certain chronic diabetic complications. The aforementioned diastereomeric ureido intermediates are novel compounds.

REFERENCES:
patent: 4117230 (1978-09-01), Sarges
patent: 4130714 (1978-12-01), Sarges
patent: 4716113 (1987-12-01), Urban
Reinhard Sarges et al., in the Journal of Organic Chemistry, vol. 47, p. 4081 (1982).
William H. Pirkle et al., in the Journal of Organic Chemistry, vol. 49, p. 2433 (1984).

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