Process for the production of biotin precursors

Details Process for the production of biotin precursors Process for the production of biotin precursors

1987-12-01

1989-07-25

Schwartz, Richard A.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548111, 548303, 549 62, 549 63, 549295, 549313, C07D491048, C07D49504

Patent

active

048515400

ABSTRACT:
Process for the production of imidazole derivatives of the formula: ##STR1## wherein R.sub.1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, R.sub.2 is hydrogen, a substituted or unsubstituted alkanoyl group, an unsubstituted or a substituted benzoyl group, a substituted or an unsubstituted benzyl group, an alkoxycarbonyl group, and aryloxycarbonyl group, an alkoxyalkyl group, a pyranyl group, a substituted or unsubstituted benzenesulfonyl group, an alkylsulfonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, and A is a sulfur or oxygen atom. A tetronic acid of the formula: ##STR2## wherein A has the above-mentioned meaning, is reacted with a diazonium salt, converting the resultant arylazotetronic acid or the tautomeric arylhydrazone in a further step with a chiral amine into an arylazoamino compound, reducing the arylazoamino compound, converting the resultant diamine, with phosgene or a phosgene-equivalent reagent, into the corresponding imidazole and optionally introducing a protective group by reaction with a substituted or unsubstituted aliphatic or aromatic acid chloride, an aliphatic or aromatic carboxylic acid anhydride, a haloformic acid alkyl ester, a 1-alkoxyalkyl halide, an enol ether, an aromatic or aliphatic sulfonic acid halide, a diarylphosphinic acid halide, a phosphoric acid dialkyl ester halide, a trialkyl silyl halide or a trialkyl silyl acetamide. These imidazole derivatives are suitable as intermediate products for the production of (+) biotin.

REFERENCES:
patent: 2489232 (1949-11-01), Goldberg et al.
patent: 2489235 (1949-11-01), Goldberg et al.
patent: 4054740 (1977-10-01), Field
Tanaka et al., Chem. Pharm. Bull., vol. 32, No. 8, pp. 3291-3298 (1984).

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