Process for the manufacture of 3-keto-6-azido-4,6-bis-dehydro-st

Details Process for the manufacture of 3-keto-6-azido-4,6-bis-dehydro-st Process for the manufacture of 3-keto-6-azido-4,6-bis-dehydro-st

Filed on

1974-06-10

Date issued

1976-01-06

Examiner

Love, Ethel G.

Patent Class

Chemistry of carbon compounds

SubClass

Miscellaneous organic carbon compounds

SubSubClass

C-metal

Other Related Categories

260349, 2603974, 26039745, 26039747, 260999, C07J 100, C07J 500

Type

Patent

Status

active

Patent number

039311678

Description

ABSTRACT:
Pharmacologically valuable 3-keto-6-azido-4,6-bis-dehydro-steroids are prepared by treating a 3-keto-6.beta.,7-diacyloxy-4-dehydro-steroid, preferably a 3-keto-6.beta.,7.beta.-diacyloxy-4-dehydrosteroid, wherein said acyloxy group is a good leaving group (e.g. hydrocarbonsulfonyloxy), with an azide salt in a nonreactive organic solvent. Novel intermediates for this process, i.e. novel 3-keto-6.beta.,7.beta.-dihydroxy-4-dehydro-steroids and 6.beta.,7.beta.-dihydrocarbonsulfonyloxy-esters thereof, are conveniently prepared by treating a 3-keto-4,6-bis-dehydro-steroid with osmium tetroxide followed by reductive cleavage of the 6.beta.,7.beta.-osmate ester thereby formed, isolating and thence esterifying the resulting 3-keto-6.beta.,7.beta.-dihydroxy-4-dehydro-steroid with a hydrocarbonsulfonyl halide in a tertiary amine.

REFERENCES:
patent: 3026320 (1962-03-01), Djerassi et al.
patent: 3665017 (1972-05-01), Teutsch et al.
patent: 3707484 (1972-12-01), Rausser et al.
Kelsy et al. Steroids, 18:3 pp. 261-279 (1971).

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