Sodium Carbonate → Oseltamivir

HRID 1773014

Reaction equation

HRID 1773014 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].P(=O)([O-])[O-].C([O-])([O-])=O.[Na+].[Na+]>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

4

Reactant 2

HCID 10340Sodium CarbonateHCID 178469146HCID 178469146, compound

Product 1

HCID 65028Oseltamivir

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of oseltamivir phosphonate (100 mg) in 50 mL DCM was treated with 50 ml aqueous Na2CO3 (60 mg). The white solution was stirred over a period of 45 minutes at room temperature. The combined aqueous and organic layers were extracted with dichloromethane (100 mL) and the organic phase was dried over Na2SO4. The combined organic phases were evaporated in a rotary evaporator to yield the product oseltamivir as a liquid, which was used without further purification in the next step. Oseltamivir amine was

Workup

  1. extractionThe combined aqueous and organic layers were extracted with dichloromethane (100 mL)
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customThe combined organic phases were evaporated in a rotary evaporator

Sources & evidence

ORD record
ord-6b928a25700d47eca71c698550f86623
Source dataset
uspto-grants-2016_02
Patent number
US09250238B2

Linked notes

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