Reaction #43885

ord-db3afd7ac0164b48b415eb3b440f1a36

Reaction equation

O=C(O)C(O)C(O)C(=O)O
Tartaric acid
CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
oseltamivir
→
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
Yield 97.6%

Reactants

O=C(O)C(O)C(O)C(=O)O
Tartaric acid
CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
oseltamivir

Reagents

None

Solvents

CCOC(C)=O
ethyl acetate

Conditions

Temperature
50°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureslowly cooled to 30° C. in 1 hour
  2. 2
    FiltrationFiltered the solid
  3. 3
    Washwashed with 70 ml of ethyl acetate
  4. 4
    Otherdried

Procedure

Tartaric acid (5 gm) is added to the solution of oseltamivir free base (9 gm, HPLC purity: 95.8%) in ethyl acetate (50 ml) at 25-30° C., the contents are heated to 50° C. and then slowly cooled to 30° C. in 1 hour. Filtered the solid, washed with 70 ml of ethyl acetate and dried to yield 13 gm of oseltamivir tartrate (HPLC purity: 97.2%).

Source

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