Sodium Hydroxide → 4-{[(4-Biphenylyloxy)acetyl]amino}-3-thiophenecarboxylic acid

HRID 14593Notes

Reaction equation

HRID 14593 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:26])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].[OH-].[Na+]>C(O)C>[C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:14]([O: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:26])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24886422Methyl 4-{[(4-biphenylyloxy)acetyl]amino}-3-thiophenecarboxylate

Product 1

HCID 117031034-{[(4-Biphenylyloxy)acetyl]amino}-3-thiophenecarboxylic acidYield 104.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-[2-(biphenyl-4-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (100 mg, 0.259 mmol) in ethanol (6 mL) was added a solution of sodium hydroxide (1N, 0.41 mL, 0.41 mmol) and the reaction was stirred at room temperature for 30 hours. After such time the reaction mixture was filtered through glass wool and the filtrate was then neutralized by addition of a solution of hydrochloric acid (1N, 0.39 mL). The precipitate was filtered, washed with water and dried in vacuo to yield the title compound as a white solid (96 mg, 80%).

Workup

  1. filtrationAfter such time the reaction mixture was filtered through glass wool
  2. additionthe filtrate was then neutralized by addition of a solution of hydrochloric acid (1N, 0.39 mL)
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-625a92c473c249fa9b471dd4bd97d822
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

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