2,3-Dihydroxybutanedioic Acid → Oseltamivir tartrate

HRID 15607

Reaction equation

HRID 15607 reaction equation
[C:1]([OH:10])(=[O:9])[CH:2]([CH:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH3:11][CH2:12][CH:13]([O:16][C@H:17]1[C@H:22]([NH:23][C:24]([CH3:26])=[O:25])[C@@H:21]([NH2:27])[CH2:20][C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18]1)[CH2:14][CH3:15]>C(OCC)(=O)C>[CH3:15][CH2:14][CH:13]([O:16][C@H:17]1[C@H:22]([NH:23][C:24]([CH3:26])=[O:25])[C@@H:21]([NH2:27])[CH2:20][C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:18]1)[CH2:12][CH3:11].[CH:2]([OH:3])([C:1]([OH:10])=[O:9])[CH:4]([OH:5])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 65028Oseltamivir

Product 1

HCID 16667738Oseltamivir tartrateYield 97.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

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%).

Workup

  1. temperatureslowly cooled to 30° C. in 1 hour
  2. filtrationFiltered the solid
  3. washwashed with 70 ml of ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-db3afd7ac0164b48b415eb3b440f1a36
Source dataset
uspto-grants-2010_06
Patent number
US07732632B2

Linked notes

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