Phenoxyacetyl chloride Penicillin

In the course of their studies on the synthesis of ot-amido-spiro-(5-lactams as analogs of penicillin and cephalosporin, Manhas et al. [76] have prepared 1-phenyl-3-phenoxy-4,4-spirocyclohexylazetidin-2-ones by the reaction of phenoxyacetyl chloride 7 and cyclohexylidenephenylamine 8 in the presence of triethylamine and dichloromethane. Azidoacetyl chloride was found to be even more reactive... 

A soln. of phenoxyacetyl chloride in acetone added during 10 min. with stirring and ice-cooling to a soln. of D-a-6-aminopenicillanic acid in 4%-KHG03-soln. and acetone, stirring continued 30 min. at room temp. -> penicillin V. Y 80% as the K-salt. F. e. s. J. G. Sheehan and K. R. Henery-Logan, Am. Soc. 84, 2983 (1962). 

Phosphorus pentachloride has often been used to remove amido side chains in the cephalosporin and penicillin series (Fechtig et al., 1968 Chauvette et al., 1971, 1972). This reaction proceeds through imino chlorides which are subsequently hydrolyzed to amines. Researchers at Lilly laboratories found (Lunn et al., 1974) that reaction of cephamycin diesters 428 and 429 with phosphorus pentachloride in pyridine-methylene chloride for 1 hr at 25°C also formed imidoyl chlorides (430). To exploit the interesting observation that alcohols are capable of converting imidoyl chlorides directly to amines, 430 was treated with methanol and subsequently with phenoxyacetyl chloride (pyridine). 7-Amido-7-methoxy-cephalosporins were isolated in 40% yield as a mixture of C-7 epimers (433 and 434). These materials can be distinguished from each other by the H-NMR signal of the C-6 proton. The ratio of 7a- to 7p-methoxy... 

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