Hydrochloric Acid → 3-Chloro-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carboxylic acid

HRID 1952598Notes

Reaction equation

HRID 1952598 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11](=[O:28])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][Si](C(C)(C)C)(C)C)[CH:15]=2)=[CH:8][C:9]=1[Cl:10])=[O:4].O.[OH-].[Li+].C1COCC1.Cl>O>[Cl:10][C:9]1[CH:8]=[C:7]([C:11](=[O:28])[NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 682270485-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-chloro-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682265653-Chloro-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[3-(tert-Butyl-dimethyl-silanyloxy)-benzylcarbamoyl]-3-chloro-thiophene-2-carboxylic acid methyl ester (260 mg, 0.59 mmol), lithium hydroxide monohydrate (500, mg, 11.82 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, 230 mg (100%). MS m/e 311.9 (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-3683994cc2254cbd800930f1c4fddb16
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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