Citric Acid → L 674573

HRID 1029444Notes

Reaction equation

HRID 1029444 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([S:29][CH2:30][C:31]([O:33]C)=[O:32])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([S:29][CH2:30][C:31]([OH:33])=[O:32])[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:15][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 86745621{[4-Phenyl-1-(4-(2-quinolinylmethoxy)phenyl)butyl]thio}acetic acid, methyl ester

Product 1

HCID 124437L 674573

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the ester (Step III) in 20 mL of THF/MeOH (1:1) was added NaOH (6 mL, 1M). After 1 h at RT, the reaction was acidified with aqueous citric acid and the organic phase was partially evaporated. The solid was filtered off, washed with water and recrystallized from ethyl acetate/hexane to afford the title compound. m.p. 141°-143°.

Workup

  1. customthe organic phase was partially evaporated
  2. filtrationThe solid was filtered off
  3. washwashed with water
  4. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-26fdc166495340219cfb9240d16ca8c2
Source dataset
uspto-grants-1992_04
Patent number
US05102881

Reaction notes

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