new intermediates for the manufacture of penicillin or cephalosporin and procedures in their production and process for the manufacture of penicillins or cephalosporins or derivatives thereof from these intermediates

摘要

1459999 Silylated penicillins and cephalosporins; precursors NOVO INDUSTRI A/S 21 Dec 1973 [27 Dec 1972 30 April 1973 8 Oct 1973] 59708/72 20526/73 and 46953/73 Heading C3S [Also in Division C2] The invention comprises compounds of formula wherein R is trialkylsilyl ; X is selected from where RSP1/SP is H or acetoxy; and P-is selected from where QSP1/SP and QSP2/SP are each O or S, RSP2/SP is H or alkyl, and n is 1 or 2; their preparation (i) from the corresponding free amines by reaction with P-halogen, or (ii) from the corresponding compounds where R is a secondary or tertiary ammonium radical by reaction with a trialkylsilyl halide; and their conversion into compounds of formula wherein RSP3/SP is an organic group and RSP4/SP is trialkylsilyl by reaction with a compound containing a CORSP3/SP group. The internal anhydride of D(-)-p-trimethylsiloxy - N - carboxy - α - phenylglycine is prepared from D(-) - p - hydroxy - α - phenylglycine by the successive actions of ClSiMe 3 / Et 3 N and phosgene (Ex. 21B). Trimethylsilyl phenoxyacetate is prepared by reacting phenoxyacetic acid with ClSiMe 3 /Et 3 N (Ex. 22). The trimethylsilyl ester of N-tert-butoxycarbonyl - D(-) - α - phenylglycine is prepared from the free acid by reaction with ClSiMe 3 / Et 3 N (Ex. 23).