Synthesis of s-fluoromethyl...

Details Synthesis of s-fluoromethyl... Synthesis of s-fluoromethyl...

2007-04-24

2007-04-24

Badio, Barbara P. (Department: 1617)

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

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

Reexamination Certificate

active

10517944

ABSTRACT:
The present invention provides a convenient process for the preparation of S-fluoromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate, a compound of formula 1, comprising(a) treating 17β-[(N,N-dimethylcarbamoyl)thio]carbonyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene, a compound of formula 3 with alkali metal carbonate-alcohol system to obtain 6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioic acid, a compound of formula 4;(b) reacting the compound of formula 4 with bromofluoromethane to yield the compound of formula 1.

REFERENCES:
patent: 4335121 (1982-06-01), Phillipps et al.
patent: 2 088 877 (1982-06-01), None
patent: 109656 (1998-02-01), None
patent: 01/62722 (2001-08-01), None
Gordon H. Phillipps et al, Journal of Medicinal Chemistry 37, 3717-3729 (1994).

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