Sodium Carbonate → N-[1-((1R,2S)-2-Dibenzylamino-1-hydroxy-3-phenyl-propyl)-pent-4-enyl]-acrylamide

HRID 1436731Notes

Reaction equation

HRID 1436731 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7](Cl)(=[O:10])[CH:8]=[CH2:9].[NH2:12][CH:13]([CH2:39][CH2:40][CH:41]=[CH2:42])[C@@H:14]([OH:38])[C@@H:15]([N:23]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[CH2:24]([N:23]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C@@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:14]([CH:13]([NH:12][C:7](=[O:10])[CH:8]=[CH2:9])[CH2:39][CH2:40][CH:41]=[CH2:42])[OH:38])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 13140Acryloyl chlorideHCID 69017314(2S,3R)-4-Amino-2-dibenzylamino-1-phenyloct-7-en-3-ol

Product 1

HCID 69016262N-[1-((1R,2S)-2-Dibenzylamino-1-hydroxy-3-phenyl-propyl)-pent-4-enyl]-acrylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add sodium carbonate (0.324 g, 3.96 mmol) and acryloyl chloride (356 mg, 3.96 mmol) to a solution of (2S,3R)-4-Amino-2-dibenzylamino-1-phenyloct-7-en-3-ol (1.5 g, 3.6 mmol) in dichloromethane. Stir the reaction overnight. Concentrate under reduced pressure. Purify on silica gel with hexane/ethyl acetate mixtures to give a mixture of two products (0.8 g, 48%).

Workup

  1. customthe reaction overnight
  2. concentrationConcentrate under reduced pressure
  3. customPurify on silica gel with hexane/ethyl acetate
  4. customto give

Sources & evidence

ORD record
ord-a5e9121d029242ce830b0fa38249d571
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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