GB1312030A - Penicillin compounds and a method of synthesising same - Google Patents

Abstract

1312030 Penicillin compounds INSTYTUT PRZEMYSLU FARMACEUTYZNEGO 17 Dec 1971 [22 Dec 1970] 58618/71 Heading C2A [Also in Division C3] The invention comprises penicillin compounds of the general Formula I wherein R represents a substituted or an unsubstituted alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a heterocyclic group or a hydrogen atom; R<SP>1</SP> and R<SP>2</SP>, the same or different, represent a substituted or an unsubstituted alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a hydrogen atom or R<SP>1</SP> and E<SP>2</SP> together form a heterocyclic group; and X represents an hydroxyl group or an OR<SP>3</SP> group wherein R<SP>3</SP> represents a substituted silyl group, a substituted or an unsubstituted alkyl group, an aryl group, an aralkyl group or a cycloalkyl group. The group R<SP>3</SP> may be selected from trimethylsilyl, substituted dimethylsilyl, methyl, ethyl, propyl, butyl, benzyl, #,#,#-trichlorethyl, methoxymethyl, phenacyl, p-bromophenacyl, cyanmethyl, nitrophenyl, acetoxymethyl, propionyloxymethyl and pivaloyloxymethyl. A method of synthesizing a penicillin compound of Formula I comprises chlorinating a 6-acylaminopenicillanic acid compound of general Formula II in the presence of an anhydrous organic solvent immiscible with water and of a tertiary amine to form an imidochloride of general Formula III by means of ammonia or an amine of general Formula IV The pencillin may be isolated as a salt of an acid, e.g. hydrochloric, phosphoric, p-toluenesulphonic, citric, oxalic and tartaric acids. The chlorination reaction may be effected by PCl 5 , PCl 3 , POCl 3 , SOCl 2 , (COCl) 2 or COCl 2 at temperatures within the range - 50‹ to + 20‹ C.