Hydrochloric Acid → 5-(3-Hydroxy-benzylcarbamoyl)-3-isopropyl-thiophene-2-carboxylic acid

HRID 1952617Notes

Reaction equation

HRID 1952617 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:13](=[O:23])[NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=[O:4].O.[OH-].[Li+].C1COCC1.Cl>O>[OH:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][NH:14][C:13]([C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([CH:10]([CH3:12])[CH3:11])[CH:8]=1)=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 682265555-(3-Hydroxy-benzylcarbamoyl)-3-isopropyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682270985-(3-Hydroxy-benzylcarbamoyl)-3-isopropyl-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(3-Hydroxy-benzylcarbamoyl)-3-isopropyl-thiophene-2-carboxylic acid methyl ester (70 mg, 0.21 mmol), lithium hydroxide monohydrate (89 mg, 2.10 mmol), THF (5 mL) and water (5 mL) was stirred 15 h, acidified with 1N HCl and extracted with EtOAc (×3). The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and evaporated to give the title compound, 71.8 mg (100%). MS m/e 319.9 (M+H+).

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-88ac2941e3d642e39c682f4b655b94e1
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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