Hydrochloric Acid → 5-[(2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid

HRID 1952602Notes

Reaction equation

HRID 1952602 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:14](=[O:27])[NH:15][CH2:16][C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][C:20](=[O:26])[NH:21]3)=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])=[O:4].O.[OH-].[Li+].C1COCC1.Cl>O>[O:26]=[C:20]1[CH2:19][C:18]2[C:22](=[CH:23][CH:24]=[CH:25][C:17]=2[CH2:16][NH:15][C:14]([C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([C:10]([F:13])([F:11])[F:12])[CH:8]=2)=[O:27])[NH:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 682267015-[(2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682268215-[(2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[(2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carboxylic acid methyl ester (270 mg, 0.68 mmol), lithium hydroxide monohydrate (280 mg, 6.77 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, 260 mg (99%). MS m/e 354.9 (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-6bfba90f9048442080b35567accb0eb8
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

Loading…