Lithium hydroxide, monohydrate → 4-[4-(2-Chloro-phenoxy)-butyrylamino]-thiophene-3-carboxylic acid

HRID 14601Notes

Reaction equation

HRID 14601 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:23])[CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:8][S:7][CH:6]=1)=[O:4].O.[OH-].[Li+]>O1CCCC1.O>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH2:14][CH2:13][CH2:12][C:11]([NH:10][C:9]1[C:5]([C:3]([OH:4])=[O:2])=[CH:6][S:7][CH:8]=1)=[O:23]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 686879784-[4-(2-Chloro-phenoxy)-butyrylamino]-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 160681514-[4-(2-Chloro-phenoxy)-butyrylamino]-thiophene-3-carboxylic acidYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[4-(2-Chloro-phenoxy)-butyrylamino]-thiophene-3-carboxylic acid methyl ester (270 mg, 0.763 mmol) was added to a solution of lithium hydroxide monohydrate (71.1 mg, 1.68 mmol) in a mixture of tetrahydrofuran (7.4 mL) and water (7.4 mL) and the reaction mixture was stirred for 3 hours at room temperature. The tetrahydofuran was evaporated and the solution was 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 yellow solid (218 mg, 84%).

Workup

  1. customThe tetrahydofuran was evaporated
  2. additionthe solution was 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-85204229f23a4976b5bbc6d553ebab1c
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

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