Process for epimerizing beta-lactam antibiotic compounds, and re

Details Process for epimerizing beta-lactam antibiotic compounds, and re Process for epimerizing beta-lactam antibiotic compounds, and re

1977-05-19

1979-09-11

Daus, Donald G.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

2602453, 544 20, 544 19, 544282, 544229, 546183, C07D26352, C07D23970, C07D26512, C07D22102

Patent

active

041676300

ABSTRACT:
Through total synthesis methods developed in the assignee's laboratories, new as well as old penicillin and cephalosporin compounds (all containing the beta-lactam functional group) have been prepared. One of the key intermediates prepared by total synthesis has the 7-amino (6-amino in the case of a penicillin derivative) group in the alpha configuration. The instant invention provides a general route for preparing the 7.beta.-amino (or 6.beta.-amino) compound, through the formation of an imino-containing intermediate, followed by hydrolysis to the desired epimer. Novel intermediate products are provided. The compounds having the desired beta epimer can be converted to acylaminoantibiotics.

REFERENCES:
patent: 3719667 (1973-03-01), Gutowski
Morrison, et al., Organic Chemistry, Sec. Ed. 1966, Allyn and Bacon, Inc., Boston, pp. 989-994.

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