Process for preparing aminohydroxycephamcarboxylates

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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540222, C07D50120

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active

046476580

ABSTRACT:
A useful synthetic intermediate, 7-amino-3-acyloxycepham-4-carboxylic acid aralkyl ester, is prepared by reducing 7-amido-3-oxocepham-4-carboxylic acid aralkyl ester with alkali metal borohydride in a dry organic solvent at temperature lower than -20.degree. C. and then acylating the resulting 3-hydroxycepham compound with an acylating reagent to give 3-acyloxycepham compound, and then subjecting the 3-acyloxycepham compound to amide cleavage consisting of treatments (1) with a mixture of phosphorus pentachloride and aromatic base giving imino-chloride and (2) with alcohol for converting the latter into imino-ether and for subjecting the product to alcoholysis giving the objective compound.

REFERENCES:
patent: 3989695 (1976-11-01), Scartazzini

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