Synthesis of Penicillin V

Structure of Penicillin V

C17H20N2O5S

Principal investigatorJohn C. Sheehan
Publication year1957
Synthesis typeTotal
Number of steps 5 (linear)
References
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