Water → HCID 21085168, compound

HRID 349016Notes

Reaction equation

HRID 349016 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-a5ddd64a0664425ea85f8d23d2eec67d
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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