Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorYujiro Hayashi
Publication year2009
Synthesis typeTotal
Number of steps 8 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure + intermediate structure
ClCH2CO2H
CH2Cl2
0 °C to RT, 3.5 h
intermediate structure
p-MePhSH
EtOH
-15 °C, 36 h, 70% (2 steps)
intermediate structure
CF3CO2H
CH2Cl2
RT, 2 h
intermediate structure
(COCl)2, DMF
CH2Cl2
0 °C to RT, 60 min
intermediate structure
NaN3
Acetone, H2O
0 °C, 20 min
intermediate structure
Ac2O
AcOH
RT, 49 h
intermediate structure
Zn, TMSCl
EtOH
70 °C, 2 h
intermediate structure
NH3, K2CO3
EtOH
0 °C to RT, 6 h, 82% (6 steps)
intermediate structure