Beta-lactam compound and preparation thereof

Details Beta-lactam compound and preparation thereof Beta-lactam compound and preparation thereof

1987-01-06

1988-12-13

Berch, Mark L.

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

Organic compounds

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

556443, C07D20508, C07F 718

Patent

active

047911980

ABSTRACT:
The present invention relates to .beta.-lactam compound having the formula (I): ##STR1## wherein R.sup.1 is a trialkylsilyl group, dimethyl-1,1,2-trimethylpropylsilyl group, acetyl group, benzyloxycarbonyl group, O-nitrobenzyloxycarbonyl group, p-nitrobenzyloxycarbonyl group or t-butyl group, R.sup.2, R.sup.3 and R.sup.4 are a member selected from the group consisting of a lower alkyl group having 1 to 6 carbon atoms, phenyl group and an aralkyl group and a process for preparing the compound which comprises reacting enolsilylethers having the formula (III): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as above, with chlorosulfonylisocyanate and then reducing the obtained product. The .beta.-lactam compound of the present invention is a useful intermediate for preparing carbapenem .beta.-lactam compound.

REFERENCES:
patent: 4474793 (1984-10-01), Ross et al.
Chiba et al, Chemistry Letters, pp. 1927-1930, 1984.
Yoshida et al, 2-(Alkylthio)penem-3-carboxylic Acids, IV,.sup.(1) Synthesis of (Hydroxyethyl)-azetidinone Precursors to 1-Thia Analogs of Thienamycin.sup.(2)), Chem. Pharm. Bull., vol 29, pp. 2899-2909, 1981.
Shiozaki et al, Stereocontrolled Syntheses of Chiral and Racemic Key Intermediates to Thienamycin from D-Allo-Threonine and Trans-Crotonic Acid.sup.(1), Tetrahedron, vol. 39, pp. 2399-2407, 1983.
Reider et al, Total Synthesis of Thienamycin: A New Approach from Aspartic Acid, Tetrahedron Letters, vol. 23, pp. 2293-2296, 1982.
Notiz uber eine verbesserte Methode zur spezifischen Freisetzung oder Acylierung primarer Hydroxylgruppen ausgedend von pertrimethylsilylierten Polyolen, Chem Ber, vol. 107, pp. 721-724, 1974.
Wetter et al, Tetrahedron Letters, vol. 26, No. 45, 1985, pp. 5515-5518.

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