Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one der

Details Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one der Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one der

1987-01-06

1989-08-29

Berch, Mark L.

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

Organic compounds

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

C07D20508, C07F 718, C07B 4112

Patent

active

048618772

ABSTRACT:
A process for preparing a 4-acetoxy-3-hydroxyethylazetidin-2-one derivative having the formula (II): ##STR1## wherein R.sup.1 is a protective group for the hydroxyl group, which comprises reacting a .beta.-lactam compound having the formula (I): ##STR2## wherein R.sup.1 is as defined above, R.sup.2, R.sup.3 and R.sup.4 are a lower alkyl group having 1 to 6 carbon atoms, phenyl group or an aralkyl group and R is a protective group for N, with acetic anhydride in an organic solvent in the presence of a base, and removing the protective group for N.
4-Acetoxy-3-hydroxyethylazetidin-2-one derivatives are useful intermediates for preparing carbapenem .beta.-lactam antibiotics such as thienamycin and penem .alpha.-lactam antibiotics.

REFERENCES:
patent: 4474793 (1984-10-01), Ross et al.
Yoshida et al., Chem. Pharm. Bull., vol. 29, pp. 2899-2909, 1981.
Shiozaki et al., Tetrahedron, vol. 39, No. 13, 1983, pp. 2399-2407.
Reider et al., Tetrahedron Letters, vol. 23, No. 22, pp. 2293-2296, 1982.
Fuchs et al., Chem. Ber. 107, pp. 721-724, 1974.
Wetter et al., Tetrahedron Letters, vol. 26, No. 45, 1985, pp. 5515-5518.
Chiba et al., Chemistry Letters, No. 7, 1984, pp. 1927-1930.

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