Reaction #43886

ord-958f4ca71a0043ed81f947dbc750f7d2

Reaction equation

CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=C(O)C(O)C(O)C(=O)O
Oseltamivir tartrate
CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=C(O)C(O)C(O)C(=O)O
oseltamivir tartrate
CC(C)=O
acetone
O=P(O)(O)O
H3PO4
→
CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=P(O)(O)O
oseltamivir phosphate
Yield 56.3%

Reactants

CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=C(O)C(O)C(O)C(=O)O
Oseltamivir tartrate
CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=C(O)C(O)C(O)C(=O)O
oseltamivir tartrate
CC(C)=O
acetone
O=P(O)(O)O
H3PO4

Reagents

None

Solvents

CCO
ethanol

Conditions

Temperature
27.5°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationFiltered the solid
  2. 2
    Washwashed with 30 ml of acetone
  3. 3
    Otherdried

Procedure

Oseltamivir tartrate (13 gm, obtained in example 3) is added to acetone (150 ml) at 25-30° C., the solution of H3PO4 (3.5 gm) in 40 ml of ethanol is added to the contents and then stirred for 1 hour 30 minutes at 25-30° C. Filtered the solid, washed with 30 ml of acetone and dried to yield 6.5 gm of oseltamivir phosphate (HPLC purity: 99.8%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07732632B2uspto-grants-2010_06