Allyl bromide → HCID 69101508, compound

HRID 394026Notes

Reaction equation

HRID 394026 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([CH2:7][NH:8][C:9]([C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([C@@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23](=[O:44])[CH2:24][C:25]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:17])=[O:10])[CH2:2]1.C(=O)([O-])[O-:46].[K+].[K+].[CH2:51](Br)[CH:52]=[CH2:53]>C(#N)C.C(Cl)(Cl)Cl>[CH2:51]([N:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([CH2:7][NH:8][C:9]([C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([C@@H:18]2[CH2:22][C@@H:21]([OH:46])[CH2:20][N:19]2[C:23](=[O:44])[CH2:24][C:25]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:17])=[O:10])[CH2:2]1)[CH:52]=[CH2:53]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 10984804HCID 10984804, compound

Product 1

HCID 69101508HCID 69101508, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 37 mg of (2R)-N-((3S)-3-piperidylmethyl)-1-{(2S)-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxamide in 0.9 ml of acetonitrile, 0.0055 ml of allyl bromide and 25 mg of potassium carbonate were added at room temperature, followed by 1.5 hours' stirring at 80° C. under heating. The reaction liquid was diluted with chloroform, washed successively with water and 1N aqueous sodium hydroxide solution, and dried over anhydrous sodium sulfate. After distilling the solvent off under reduced pressure, the resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/10/1), to provide 23 mg of the title compound as a white solid.

Workup

  1. temperatureunder heating
  2. customThe reaction liquid
  3. washwashed successively with water and 1N aqueous sodium hydroxide solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling the solvent off under reduced pressure
  6. customthe resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol/28% aqueous ammonia=100/10/1)

Sources & evidence

ORD record
ord-cbf4d3c95cf64820a6faa57d34450b31
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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