Hydrochloric Acid → (RS)-Clopidogrel

HRID 1590780

Reaction equation

HRID 1590780 reaction equation
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[C:11]([O:13][CH3:14])=[O:12].[CH2:22]=O>C(Cl)Cl>[S:2]1[C:3]2[CH2:7][CH2:8][N:9]([CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:11]([O:13][CH3:14])=[O:12])[CH2:22][C:4]=2[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10223136Methyl [2-(2-thienyl)ethylamino](2-chlorophenyl)acetate

Product 1

HCID 2806(RS)-Clopidogrel

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

35 g of the hydrochloride of racemic methyl alpha-(2-thienylethylamino)(2-chlorophenyl)acetate are suspended in 150 ml of a 30% (w/w) aqueous solution of formaldehyde. The mixture is kept at 50° C. for 2 hours and then poured, at about 20° C., into 200 ml of methylene chloride. The organic phase is concentrated and the residual oil is dissolved in 120 ml of isopropyl ether in which the hydrochloride is prepared as before; 29.5 g are obtained.

Workup

  1. concentrationThe organic phase is concentrated
  2. dissolutionthe residual oil is dissolved in 120 ml of isopropyl ether in which the hydrochloride
  3. customis prepared as before
  4. custom29.5 g are obtained

Sources & evidence

ORD record
ord-f5c9992b4803468f97c3f790d71a0507
Source dataset
uspto-grants-1993_04
Patent number
US05204469

Linked notes

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