Acyloxylation process for preparing 4-acyloxy-2-azetidinone deri

Details Acyloxylation process for preparing 4-acyloxy-2-azetidinone deri Acyloxylation process for preparing 4-acyloxy-2-azetidinone deri

1995-07-24

1997-06-17

Berch, Mark L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07D20508, C07B 4112

Patent

active

056398786

ABSTRACT:
The present invention relates to a novel and improved process for preparing 4-acyloxy-2-azetidinone derivatives having the following formula (I) which are useful as an intermediate for synthesis of penem or carbapenem compounds: ##STR1## in which R.sub.1 represents a hydroxy-protecting group; and R.sub.3 represents an acyl group, which comprises reacting an azetidinone derivative having the following formula (II): ##STR2## wherein R.sub.1 is defined as above and R.sub.2 represents an alkyl group or an aryl group, with a N-haloacylimide in the presence of an organic carboxylic acid or a salt of an organic carboxylic acid.
The present invention uses the organic compound, N-haloacylimide, as the reactant rather than the heavy metal reactant used in the prior art, and thus provides an economical advantage and does not cause any problem related to safety and waste disposal after the reaction.

REFERENCES:
Brain, J.C.S. Chem Comm 1972, p. 229.
Tetrahedron Letters, vol. 22, No. 51, pp. 5205-5208, 1981 (Shiozaki et al.).
Tetrahedron Letters, vol. 30, No. 41, pp. 5631-5634, 1989 (Ito).
Tetrahedron Letters, vol. 23, No. 22, pp. 2293-2296, 1982 (Neider).
J. Am. Chem. Soc. 1990, 112, pp. 7820-7822 Murahashi.
Chem. Pharm, Bull. 29(10) 2899-2909 (1981) (Yoshida et al.).

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