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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D501-24
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filingDate 1971-03-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1973-01-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber ES-377938-A1
titleOfInvention PROCEDURE TO PREPARE 3 - HALOGENOMETIL - DELTA - CEPHALOSPORIN ESTERS OR SULFOXIDES THEM
abstract Procedure for preparing 3-halogenomethyl-Delta3-cephalosporin or sulfoxide esters thereof, useful as intermediates in the production of antibiotics, and represented by the formulas **(See formula)** where X in each of formulas I and II is chlorine, bromine or iodine; R has the formula **(See formula)** where m is an integer from 0 to 4, n is an integer from 1 to 4, Z is oxygen or sulfur or a chemical bond, R3 and R4 are separately hydrogen or methyl, and Y is hydrogen or a substituent on carbon atoms of the phenyl ring such as fluorine, chlorine, bromine, iodine, C1 to C2 alkyl, C1 to C2 alkyloxy, N-protected alpha-aminoalkyl of C1 to C3, butoxycarbonyl, nitro, cyano, trifluoromethyl and Z is an integer from 1 to 2; and R1 is 2,2,2-trichlorethyl, C4 to C6 tertiary alkyl, C5 to C7 tertiaryalkenyl, C5 to C7 tertiaryalkynyl, benzyl, methoxybenzyl, nitrobenzyl, phenacyl, phthalimidomethyl, or succinimidomethyl; said process being characterized by reacting a phosphorous compound from groups (1) phosphorous trichloride or phosphorous tribromide, or (2) phosphorous pentachloride, phosphorous pentabromide, phosphorous oxychloride or phosphorous oxybromide with a 3-sulfoxide ester -hydroxymethyl-Delta3-cephalosporin, in the presence of a tertiary amine in a substantially anhydrous liquid diluent, at a temperature of about -75ºC to about 50ºC to form the corresponding (1) (a) ester of 3-halogenomethyl-Delta3- cephalosporin from at least an equimolar amount of phosphorous trichloride or phosphorous tribromide, when temperatures above about -25ºC or (1) (b) 3-halogenomethyl-Delta3-cephalosporin sulfoxide ester are used from a approximately equimolar amount of phosphorous tribromide or phosphorous trichloride, when temperatures below about -25ºC or (2) ester are used of 3-halogenomethyl-Delta3-cephalosporin sulfoxide from phosphorous pentachloride, phosphorous pentabromide, phosphorous oxychloride or phosphorous oxybromide. (Machine-translation by Google Translate, not legally binding)
priorityDate 1969-03-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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