Ammonia → Oseltamivir

HRID 15606

Reaction equation

HRID 15606 reaction equation
[CH3:1][CH2:2][CH:3]([O:6][C@H:7]1[C@H:12]([NH:13][C:14]([CH3:16])=[O:15])[C@@H:11]([NH2:17])[CH2:10][C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8]1)[CH2:4][CH3:5].OP(O)(O)=O.O.N>C(Cl)Cl>[CH3:5][CH2:4][CH:3]([O:6][C@H:7]1[C@H:12]([NH:13][C:14]([CH3:16])=[O:15])[C@@H:11]([NH2:17])[CH2:10][C:9]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8]1)[CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 78000Tamiflu

Product 1

HCID 65028OseltamivirYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oseltamivir phosphate (20 gm, HPLC purity: 97%) is stirred with water (100 ml) and methylene chloride (100 ml) for 10 minutes at 25-30° C. and then pH of the mass is adjusted to 9-10 with liquor ammonia. Separated the layers, the organic layer is subjected to carbon treatment and filtered on hiflo bed. Washed the hiflo bed with methylene chloride (20 ml) and then distilled the organic layer under vacuum at 40° C. to give 16.5 gm of oseltamivir free base as a residue.

Workup

  1. customSeparated the layers
  2. filtrationfiltered on hiflo bed
  3. washWashed the hiflo bed with methylene chloride (20 ml)
  4. distillationdistilled the organic layer under vacuum at 40° C.

Sources & evidence

ORD record
ord-950cdd41c55d4453b1774526ef2cfe7b
Source dataset
uspto-grants-2010_06
Patent number
US07732632B2

Linked notes

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