Potassium Acetate → HCID 22627519, compound

HRID 1108708Notes

Reaction equation

HRID 1108708 reaction equation
Br[CH:2]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:8]=2)[CH2:3][CH3:4].[C:23]([O-:26])(=[O:25])[CH3:24].[K+]>C(O)(=O)C>[C:23]([O:26][CH:2]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=[C:9]([C:19]([O:21][CH3:22])=[O:20])[CH:8]=2)[CH2:3][CH3:4])(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 22627433HCID 22627433, compound

Product 1

HCID 22627519HCID 22627519, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-(1-bromopropyl)-3-isobutyrylindole-6-carboxylate (323 mg) in acetic acid (3 ml) was added potassium acetate (345 mg) and the mixture was stirred at 60° C. for 2 hours. The resulting mixture was evaporated in vacuo, then the residue was diluted with ethyl acetate and washed with water, aqueous sodium bicarbonate and brine. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (2:1) to give methyl 2-(1-acetoxypropyl)-3-isobutyrylindole-6-carboxylate (207 mg).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water, aqueous sodium bicarbonate and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-8206d341aa8348d8bdf49db4aed9c4d6
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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