Synthesis of Penicillin V

Structure of Penicillin V

C17H20N2O5S

Principal investigator	John C. Sheehan
Publication year	1957
Synthesis type	Total
Number of steps	5 (linear)
References	J. Am. Chem. Soc. 1957, 79, 1262. J. Am. Chem. Soc. 1959, 81, 3089.

Part 1 of 1

intermediate structure

+

intermediate structure

NaOAc

EtOH, H2O

RT, 10 h, 24%

"Also isolated was the C1'-epimer (30 % yield) which was equilibrated in refluxing pyridine."

intermediate structure

NH2NH2

Dioxane , H2O

RT, 24 h, 82%

intermediate structure

+

intermediate structure

Et3N

CH2Cl2

0 °C, 22 h, 70%

intermediate structure

HCl

CH2Cl2

0-5 °C, 30 h, 94%

intermediate structure

DCC, NaOH

Dioxane , H2O

RT, 33 h, 11%

intermediate structure

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