Synthesis of penicillin-V
Synthesis of Penicillin-V
Penicillin was synthesized by Sheehan et. al. in 1957-1959 who synthesized Penicillin-V.Condensation of D-penicillamine and tert-butyl α-phthalimidomalonaldehydate yields an intermediate. This on treatment with hydrazine followed by HCl gives amine hydrochloride. This amine hydrochloride on further treatment with phenoxyacetylchloride in trimethylamine introduces the side chain to yield an ester which when subjected to a stream of HCl at 0°C in pyridine gives penicilloic acid. The resulting acid undergoes cyclization to afford penicillin-V by stirring for 20 minutes with a solution of N,N'-dicyclohexylcarbodiimide in dioxane.