Sodium Hydroxide → Satigrel

HRID 1031641Notes

Reaction equation

HRID 1031641 reaction equation
[C:1]([C:3](=[C:11]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:4][CH2:5][C:6]([O:8]CC)=[O:7])#[N:2].[OH-].[Na+]>O1CCOCC1>[C:1]([C:3](=[C:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH2:4][CH2:5][C:6]([OH:8])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 30876684-Pentenoic acid, 4-cyano-5,5-bis(4-methoxyphenyl)-, ethyl ester

Product 1

HCID 65913Satigrel

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

3.6 g or ethyl 4-cyano-5,5-bis(4-methoxyphenyl)-4-pentenoate was dissolved in 10 ml of dioxane and 3 ml of a 5N aqueous solution of NaOH was added thereto. The obtained mixture was stirred at 60° C. for five hours. After the completion of the reaction, the reaction mixture was acidified and extracted with ethyl acetate. Thus 3.2 g of the title compound having the following physicochemical properties was obtained. This product could be further purified by recrystallizing form ethyl acetate/hexane.

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate
  3. customwas obtained
  4. customThis product could be further purified
  5. customby recrystallizing form ethyl acetate/hexane

Sources & evidence

ORD record
ord-582a3bd3a6f84c6cab827e92ee3d6c30
Source dataset
uspto-grants-1990_09
Patent number
US04954523

Reaction notes

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