Sulfuric Acid → Clopidogrel hydrogen sulfate

HRID 988847Notes

Reaction equation

HRID 988847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:13]1[CH2:18][CH2:17][C:16]2[S:19][CH:20]=[CH:21][C:15]=2[CH2:14]1)[C:9]([O:11][CH3:12])=[O:10].[S:22](=[O:26])(=[O:25])([OH:24])[OH:23]>>[S:22]([OH:26])([OH:25])(=[O:24])=[O:23].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:13]1[CH2:18][CH2:17][C:16]2[S:19][CH:20]=[CH:21][C:15]=2[CH2:14]1)[C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 2806(RS)-Clopidogrel

Product 1

HCID 16757820Clopidogrel hydrogen sulfate

Procedure

10 g of (+) Methyl (2-chlorophenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetate prepared according to Example 22, was dissolved in 100 mL of ice-cold acetone and 2 mL concentrated sulfuric acid was added at 0° C. to 5° C. The crystalline white to off white product formed was isolated by filtration and washed with 20 mL of acetone. The product obtained was dried in vacuum oven at 50° C. The yield of titled product was 7.2 g (56%).

Workup

  1. customThe crystalline white to off white product formed
  2. customwas isolated by filtration
  3. washwashed with 20 mL of acetone
  4. customThe product obtained
  5. customwas dried in vacuum oven at 50° C

Sources & evidence

ORD record
ord-36cdd97f1ee749908319609117fb96ed
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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