Acetic Acid → HCID 22346150, compound
Reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([CH:17]([NH:20][CH2:21][CH2:22][NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:18][CH3:19])[CH3:16].[CH3:34][CH:35]([CH3:39])[CH2:36]C=O.C(O)(=O)C>ClCCl>[CH2:15]([CH:17]([N:20]([CH2:34][CH:35]([CH3:39])[CH3:36])[CH2:21][CH2:22][NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:18][CH3:19])[CH3:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium triacetoxyborohydride (1.87 g, 8.84 mmol) was added to a solution of benzyl 2-[(1-ethylpropyl)amino]ethylcarbamate (1.8 g, 6.8 mmol) (Preparation 50), 3-methylbutanal (0.8 ml, 7.5 mmol) and acetic acid (1 ml, 8.85 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with dichloromethane (50 ml) and then washed with saturated aqueous sodium hydrogen carbonate solution (100 ml). The organic phase was dried over anhydrous magnesium sulphate and then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume). This gave the title compound as an oil (1.3 g).
Workup
- washwashed with saturated aqueous sodium hydrogen carbonate solution (100 ml)
- dry with materialThe organic phase was dried over anhydrous magnesium sulphate
- customthe solvent was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (95:5 by volume)
- temperatureincreasing in polarity to dichloromethane
Sources & evidence
- ORD record
- ord-74cfb185714540f98ca4f9d739cf23f6
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921753B2
Reaction notes
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