Potassium Carbonate → HCID 53847566, compound

HRID 850676Notes

Reaction equation

HRID 850676 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[CH:18]=1)=[C:11]2[C@H:25]([CH3:28])[CH2:26][NH2:27])([CH3:7])[CH3:6])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].C([N+]1(C)[CH2:44][CH2:43][C:42](=[O:45])[CH2:41][CH2:40]1)C>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:18]=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[CH:22]=1)=[C:11]2[C@H:25]([CH3:28])[CH2:26][N:27]1[CH2:44][CH2:43][C:42](=[O:45])[CH2:41][CH2:40]1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15523806Ethyl 3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-α,α-dimethyl-1H-indole-5-acetateHCID 22118984HCID 22118984, compound

Product 1

HCID 53847566HCID 53847566, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester (EXAMPLE 1, Step 1B, 0.50 g in 2 mL ethanol) was added 18 mg potassium carbonate followed by the dropwise addition of a solution of 1-ethyl-1-methyl-piperidinium-4-one chloride (513 mg in 0.80 mL water) and the mixture heated to reflux on an oil bath. After 1 hour, the mixture was cooled to room temperature, diluted with ethyl acetate and washed successively with 10% aqueous sodium bisulfate, water, saturated aqueous sodium bicarbonate and brine. The organic portion was dried over sodium sulfate, concentrated in vacuo and the residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 7:3) to give the title compound (356 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. washwashed successively with 10% aqueous sodium bisulfate, water, saturated aqueous sodium bicarbonate and brine
  4. dry with materialThe organic portion was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-b5f99b75fd0e419f83d0a6e674d97e3c
Source dataset
uspto-grants-2000_01
Patent number
US06017944

Reaction notes

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