Method of preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)2,3

Details Method of preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)2,3 Method of preparing (+)-(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)2,3

1989-09-14

1991-05-07

Bond, Robert T.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07D28102

Patent

active

050138359

ABSTRACT:
2-Aminothiophenol is reacted with (-)-(2R,3S)-2,3-epoxy-3-(4-methoxyphenyl) methylpropionate, and the intermediate (2S,3S)-3-[(2-aminophenyl)thio]-2-hydroxy-3-(4-methoxyphenyl) methylpropionate is then cyclized in the presence of methane sulfonic acid, in the same container and without isolating said intermediate product, using chlorobenzene as a solvent.

REFERENCES:
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patent: 4438035 (1984-03-01), Gaino et al.
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patent: 4885375 (1989-05-01), Wynberg et al.
Hashiyama et al. (1985), J. Chem. Soc. Perkin. Trans., 1: 421-427, Kugita et al. (1970), Chem. Pharm. Bull. 18: 2028-2037.

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