Process for preparing steroidal acids and their intermediate der

Details Process for preparing steroidal acids and their intermediate der Process for preparing steroidal acids and their intermediate der

1978-02-13

1979-10-23

Love, Ethel G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603971, 2603972, 2603974, C07J 1700, C07J 900

Patent

active

041720768

ABSTRACT:
Steroidal acids of the formula ##STR1## are prepared from steroidal ketones of the formula ##STR2## wherein R.sub.1 is hydrogen; hydroxy; lower alkyloxy; tetrahydropyranyloxy; aryloxy; alkyl; alkanoyloxy or aroyloxy; R.sub.2 is hydrogen; hydroxy; lower alkyloxy; tetrahydropyranyloxy; aryloxy; alkyl; alkanoyloxy or aroyloxy; R.sub.3 is hydrogen; hydroxy; lower alkyloxy; tetrahydropyranyloxy; aryloxy; alkyl; alkanoyloxy or aroyloxy; with the proviso that R.sub.1 and R.sub.2 together or R.sub.2 and R.sub.3 together may form a carbon-carbon bond; R.sub.4 is --(CH.sub.2).sub.n CO(CH.sub.2).sub.m CH.sub.3 ; R.sub.5 is --(CH.sub.2).sub.n+m+1 COOH; R.sub.6 is hydrogen; hydroxy; lower alkyloxy; tetrahydropyranyloxy; aryloxy; alkyl; alkanoyloxy or aroyloxy; and n is 0 to 4, m is 0 to 4 and sum of n+m is 0 to 4 in the formula (I) and (II) above and these formulas include isomers and homologs of the above mentioned compounds: by reacting 1 m of ketone with 1 to 70 m sulfur and 1 to 80 m of ammonia, primary amine or secondary amine to produce a thioamide which is then hydrolyzed to an acid. These acids are useful as intermediates in the synthesis of Vitamin D derivatives.

REFERENCES:
patent: 3786062 (1974-01-01), Schroeder et al.
patent: 3801607 (1974-04-01), Goffinet
Organic Reactions III: 83-107 (1946), (John Wiley & Sons, Inc.), pp. 100, 101 and 105.

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