Water → HCID 21085168, compound

HRID 14226Notes

Reaction equation

HRID 14226 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]CCCC)=[O:15])[CH:12]=2)[C:7]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[CH:6]1)[CH2:2][CH2:3][CH3:4].O[Li].O.C1COCC1.O>CO>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[C:7]([C:21](=[O:26])[C:22]([F:23])([F:24])[F:25])=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 21086017HCID 21086017, compound

Product 1

HCID 21085168HCID 21085168, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Butyl 1-butyl-3-(trifluoroacetyl)-1H-indole-6-carboxylate (0.277 g), LiOH.H2O (0.040 g), THF (1.5 mL), water (0.5 mL), and methanol (0.5 mL) were stirred overnight at room temperature. The solvents were then removed under reduced pressure and HCl (2N, 0.5 mL) was added to the residue. The residue was extracted with ethyl acetate, dried over magnesium sulfate, filtered, and concentrated. Chromatography on silica gel using methanol/dichloromethane (6/94) gave 1-butyl-3-(trifluoroacetyl)-1H-indole-6-carboxylic acid (0.166 g). MS (ESI+) for C15H14F3N1O3+H1 m/z 314.10 (M+H)+.

Workup

  1. customThe solvents were then removed under reduced pressure and HCl (2N, 0.5 mL)
  2. additionwas added to the residue
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eb34d9a2febf4f50a8347ec62a9712ae
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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