Process for producing carbamoyl substituted penams and carbamoyl

Details Process for producing carbamoyl substituted penams and carbamoyl Process for producing carbamoyl substituted penams and carbamoyl

1979-11-07

1982-01-12

Trousof, Natalie

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

544 16, 544 18, 544 21, 544 22, 544 28, 544 29, 544 30, 2602452R, C07D49904, C07D50102

Patent

active

043104592

ABSTRACT:
Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

REFERENCES:
patent: 3275626 (1966-09-01), Morin et al.
patent: 3997533 (1976-12-01), Kabbe et al.
patent: 4010156 (1977-03-01), Nudelman et al.
Cooper et al., Accounts of Chemical Research 6, pp. 32-40, (1973).

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