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Named reactions

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Search synthesis

Oseltamivir

"Kilogram quantities of drug substance have been prepared by this route in standard pilot plant equipment."

Chemical structure of Oseltamivir
C16H28N2O4
Author John C. Rohloff
Publication year 1998
Synthesis type Total synthesis
Number of steps 12 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
2,2-Dimethoxypropane, TsOH
Acetone
Reflux, 2 h
Chemical structure
NaOEt
EtOH
RT, 2 h
Chemical structure
MsCl, Et3N
CH2Cl2
0-5 °C, 90 min, 69% (3 steps)
Chemical structure
SO2Cl2, Pyr
CH2Cl2
-30 to -20 °C, 3.5 h, 44%
Chemical structure
3-Pentanone, HClO4
H2O
40 °C, 4-20 h, 95%
Chemical structure
BH3.Me2S, TMSOTf
CH2Cl2
-20 to -10 °C, 42 min
Chemical structure
KHCO3
EtOH, H2O
55 to 65 °C, 60 min, 64% (2 steps)
Chemical structure
NaN3, NH4Cl
EtOH, H2O
70-75 °C, 12-18 h, 86%

Selectivity : 91:09
Chemical structure
+
Chemical structure
Me3P
MeCN
RT to 38 °C, 2 h
Chemical structure
NaN3, NH4Cl
DMF
70 to 80 °C, 12-18 h
Chemical structure
Ac2O, NaHCO3
CH2Cl2, Hexane(s), H2O
RT, 60 min, 43% (3 steps)

See the Schotten-Baumann Reaction
Chemical structure
H2, Ni (Raney)
1 atm
EtOH
RT, 10-16 h, 71%
Chemical structure

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