Hydrochloric Acid → 4-[2-(4-Cyclohexyl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid

HRID 14607Notes

Reaction equation

HRID 14607 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]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1.O>[CH:20]1([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:9]3[C:5]([C:3]([OH:4])=[O:2])=[CH:6][S:7][CH:8]=3)=[O:26])=[CH:15][CH:16]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 686884524-[2-(4-Cyclohexyl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 160682644-[2-(4-Cyclohexyl-phenoxy)-acetylamino]-thiophene-3-carboxylic acidYield 71%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-[2-(4-cyclohexyl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (75 mg) in 2.5 mL of a mixture of THF:water (1.5:1) was added sodium hydroxide (0.442 mL, 1 M, 2.2 eq) and the reaction mixture was stirred for 24 hours at room temperature. Then the reaction mixture was acidified by addition of a solution of aqueous HCl (0.442 mL, 1N, 2.2 eq). The precipitate was isolated, washed with water and dried in vacuo to yield 4-[2-(4-cyclohexyl-phenoxy)-acetylamino]-thiophene-3-carboxylic acid (51 mg, 71%) as a white solid.

Workup

  1. customThe precipitate was isolated
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-55f090f5fba34238abd7c0e18c73ba97
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

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