Process for the preparation of 4-acyloxy-2-azetidinone derivativ

Details Process for the preparation of 4-acyloxy-2-azetidinone derivativ Process for the preparation of 4-acyloxy-2-azetidinone derivativ

1989-10-13

1991-06-25

Berch, Mark L.

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

Organic compounds

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

C07D205085, C07B 4112

Patent

active

050268449

ABSTRACT:
A process for producing 3-[1'-(R)-hydroxyethyl]-4-acyloxyazetidinone from 3-[1'-(R)-hydroxyethyl]-4-alkyl (or aryl) thioazetidinone using a copper salt of aliphatic or aromatic carboxylic acid is disclosed. The process is an effective route for producing 3-[1'-(R)-hydroxyethyl]-4-acyloxyazetidinone, and intermediate for synthesizing penems or carbapenems, without using a mercury salt which can cause an environmental hazard.

REFERENCES:
Chemical and Pharmaceutical Bulletin, vol. 29, No. 10, Oct. 1981, pp. 2899-2909, A. Yoshida et al.: "2-(Alkylthio)Penem-3-Carboxylic Acids. IV. Synthesis of (Hydroxyethyl)-Azetidinone Precursors to 1-Thia Analogs. . . ".
Tetrahedron Letters, vol. 27, No. 29, 1986, pp. 2315-2318, C. J. Easton et al., "Direct Introduction of a Benzoyloxy Substitutent at the C-4 Position . . . ".
The Journal of Chemical Society, Chemical Communications, 1979, pp. 485, 486, H. Matsumura et al., "Direct Introduction of a Benzoyloxy Substitutent . . . ".
Synthetic Methods of Organic Chemistry, vol. 25, 1971 p. 164, Abstract 199, W. Theilheimer; "Alpha-Ketoaldehydes from 1-Hydroxy-2-Ketothioethers".
The Journal of Organic Chemistry, vol. 48, No. 22, Nov. 4, 1983, pp. 4043-4048, M. L. M. Pennings et al.,: "Chemistry of Four-Membered Cyclic Nitrones. 5. Synthesis and Oxidation of 1-Hydroxyazetidines".
Synthetic Methods of Organic Chemistry, vol. 29, 1975, p. 121, Abstract No. 215, "Glycosides from Thioglycosides with Anomerization".
C. J. Easton, J. Chem. Soc., Perkins I, 277 (1990).
van Elburg, Hetereocycles 26, 437 (1987).
Yoshida Chem. Pharm. Bull. 29 (10) 2899-2909 (1981).
Fuchigami, Chem. Abs. 107, 153936n (1987).
Ferrholz, Chem. Abs. 86, 29377q.

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