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filingDate 1975-12-18-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1978-10-11-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1527749-A
titleOfInvention Sulphinyl halides and their preparation from penicillin sulphoxides
abstract 1527749 Azetidinyl sulphinyl chlorides ELI LILLY & CO 18 Dec 1975 [24 Dec 1974 19 Nov 1975] 51963/75 Heading C2C Compounds of formula where R<SP>1</SP> is a carboxylic acid protecting group; and R is (1) an imido group of the formula in which R 2 is C 2 -C 4 alkenylene or 1,2-phenylene; (2) an amido group of the formula in which R 3 is (a) hydrogen, C 1 -C 3 alkyl, halomethyl, benzyloxy, 4-nitrobenzyloxy, tbutyloxy, 2,2,2 - trichloroethoxy, 4 - methoxybenzyloxy or 3 - (2 - chlorophenyl) - 5 - methylisoxazol - 4 - yl; (b) the group R<SP>1</SP> in which R<SP>1</SP> is 1,4-cyclohexadienyl, phenyl or phenyl substituted with 1 or 2 halogens, protected hydroxy, nitro, cyano, trifluoromethyl, C 1 -C 4 alkyl, or C 1 -C 4 alkoxy; (c) a group of the formula R<SP>1</SP>-(O) m -CH 2 - in which R<SP>1</SP> is as defined above and m is 0 or 1; or (d) a group of the formula in which R<SP>1</SP> is as defined above; and W is protected hydroxy, or protected amino; (3) an imidazolidinyl group of the formula in which R<SP>1</SP> is as defined above and U is nitroso or acetyl; or (4) an imido group of the formula in which R<SP>1</SP> and m are as defined above, and R 4 is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or 2,2,2-trichloroethoxy, are prepared by reacting a penicillin sulphoxide of formula with an N-chloro halogenating agent at 75- 135‹ C. in an inert solvent under substantially anhydrous conditions. The compounds of Formula I in which R is R 3 CONH- are claimed per se. The penicillin sulphoxide of Formula II in which R 1 is p-nitrobenzyl and R is is prepared by ozone oxidation of the corresponding penicillin, itself obtained from 2,2,2- trichloroethyl chloroformate on p-nitrobenzyl 6 - phenoxyacetamido 2,2 - dimethylpenam - 3- carboxylate.
priorityDate 1974-12-24-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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