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

HRID 1952582Notes

Reaction equation

HRID 1952582 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:14](=[O:31])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][Si](C(C)(C)C)(C)C)[CH:18]=2)=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])=[O:4].O.[OH-].[Li+].C1COCC1.Cl>O>[OH:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][NH:15][C:14]([C:7]1[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([C:10]([F:13])([F:11])[F:12])[CH:8]=1)=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 682271015-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682267205-(3-Hydroxy-benzylcarbamoyl)-3-trifluoromethyl-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester (210 mg, 0.44 mmol), lithium hydroxide monohydrate (370, mg, 8.87 mmol), THF (4 mL) and water (4 mL) was stirred over weekend, 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, 120 mg (79%). MS m/e 346.0 (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-0287ae6aaf7e40c6a09448735fe11e9a
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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