Preparation of 1-oxapenicillins and 4-acyloxy azetidinone interm

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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2602454, 2603473, 2603477, 2603474, 544111, 544359, 2603303, C07D20508, C07D40312, C07D40912, C07D40712

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active

042083257

ABSTRACT:
The invention provides a novel process for opening the ring of 2-R-6-(1'-R.sup.1 -oxycarbonyl-2'-methyl-prop-1'-enyl)-1-oxa-3,6-diaza-4S,5R-bicyclo[3,2,0]h ept-2-en-7-one by treatment with a sulfonic acid salt thereby forming R.sup.1 2-(2'R-R-oxy-3'S-amino-4'-oxo)azetidinyl-3-methyl-2-butenoate sulfonic acid salts which can provide oxapenicillins by two different routes depending on the substituent desired on the carboxamido group of the 1-oxapenicillins. In the alternate processes, new intermediates are also provided.

REFERENCES:
patent: 3948927 (1976-04-01), Wolfe
patent: 4071512 (1978-01-01), Wolfe
Wolfe et al. I, Can. J. Chem. 50, 2894-2897 (1972).
Brain et al., Chem. Abs. 84, 150420k.
Wolfe et al. II, Tetrahedron Letters 51, 5131-5134 (1973).
Stoodley et al., J. Chem. Soc. Perkins I, 1973, 32-35.
Lattrell, Annalen der Chemie 1974 (Sep.), pp. 1361, 1362, 1373, 1374.

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