Hydrochloric Acid → 4-(5-Phenyl-pentanoylamino)-thiophene-3-carboxylic acid

HRID 14594Notes

Reaction equation

HRID 14594 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][S:7][CH:6]=1)=[O:4].[Li+].[OH-].Cl>O1CCCC1.CO>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][C:11]([NH:10][C:9]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][S:7][CH:8]=2)=[O:22])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 686887754-(5-Phenyl-pentanoylamino)-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 160680444-(5-Phenyl-pentanoylamino)-thiophene-3-carboxylic acidYield 43.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-(5-phenyl-pentanoylamino)-thiophene-3-carboxylic acid methyl ester (50 mg, 0.16 mmol) in tetrahydrofuran/methanol 2/1 (1.5 ml) was added a 1 N aqueous LiOH solution (0.95 ml, 0.95 mmol). The reaction mixture was stirred at room temperature for 2 h, acidified with 1 N HCl and extracted two times with ethyl acetate. The combined organic layers were washed with water and brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by thin layer chromatography (SiO2, dichloromethane) to give the title compound as colorless oil (20 mg, 0.07 mmol, 42%).

Workup

  1. extractionextracted two times with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by thin layer chromatography (SiO2, dichloromethane)

Sources & evidence

ORD record
ord-bcbdfeb5c2c8411faccfa2cce2abe3a4
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

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