Preparation of .beta.-lactams and intermediates therefor

Details Preparation of .beta.-lactams and intermediates therefor Preparation of .beta.-lactams and intermediates therefor

1979-12-31

1981-04-07

Randolph, John D.

Harness for working animal

260239A, 2603473, 546275, C07D48704

Patent

active

042607434

ABSTRACT:
Novel process for the preparation of .beta.-lactams of the formulae: ##STR1## wherein R' represents lower alkyl, aryl or aryl (lower alkyl), R" represents hydrogen or lower alkyl or R' and R" together with the carbon atoms to which they are attached represent lower cycloalkyl, R'" represents lower alkyl or a group --OR, wherein R represents lower alkyl, X.sub.1, Y.sub.1 and Z.sub.1 are hydrogen or selected organic radicals and R.sub.1 represents an acyl group; which successively involves reacting an 1,3-dicarbonyl compound of the formula: ##STR2## with glycine in the presence of a base to form a vinylamino salt of the formula: ##STR3## wherein M.sub.1.sup.+ is the cation of the base, activating the carboxyl group of said vinylamino salt with an appropriate activating agent and reacting the activated compound in the presence of a tertiary base with an imino compound of the formula: ##STR4## to form the corresponding .alpha.-vinylamino-.beta.-lactam of formula IV A and if desired, subjecting said .beta.-lactam to mild acid hydrolysis to obtain the corresponding .alpha.-amino-.beta.-lactam of formula V A and if desired, acylating said .alpha.-amino-.beta.-lactam with an appropriate acylating agent to obtain a corresponding .alpha.-acylamino-.beta.-lactam of formula VI A.

REFERENCES:
patent: 3546211 (1970-12-01), Bose
patent: 3943123 (1976-03-01), Bose
patent: 4207234 (1980-06-01), Kamiya et al.
Sharma et al. I Tetrahedron Letters, No. 14, pp. 1265-1266 (1979).
Sharma et al. II Tetrahedron Letters, No. 46, pp. 4587-4590 (1978).

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