Triethylamine → HCID 54569758, compound
Reaction equation
[NH2:1][C@@H:2]([CH3:18])[C:3]([NH:5][C:6]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:15]([CH3:17])[CH3:16])=[O:4].[CH:19](Br)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(#N)C>[CH3:16][CH:15]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH:12]([CH3:13])[CH3:14])[C:6]=1[NH:5][C:3](=[O:4])[C@@H:2]([NH:1][CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:18])[CH3:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of (S)-2-amino-N-[2,6-bis(1-Methylethyl)phenyl]propanamide (5.0 g, 20 mmol), benzhydryl bromide (5.0 g, 20 mmol), and triethylamine (2.8 mL, 20 mmol) in acetonitrile (100 mL) was heated under reflux for 5 hours. The resulting solution was cooled (25° C.) and concentrated in vacuo. The residue was taken up in ethyl acetate (300 mL), washed with water (1×100 mL), washed with saturated sodium bicarbonate (1×100 mL), washed with brine (1×100 mL), then dried (MgSO4) and concentrated in vacuo. The resulting solid was recrystallized from ether/hexane to yield 4.77 g (57.1%) of the title compound as fine white needles, mp 134°-138.5° C.
Workup
- temperatureunder reflux for 5 hours
- concentrationconcentrated in vacuo
- washwashed with water (1×100 mL)
- washwashed with saturated sodium bicarbonate (1×100 mL)
- washwashed with brine (1×100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe resulting solid was recrystallized from ether/hexane
Sources & evidence
- ORD record
- ord-89ba7f5036974a4e92ec6e76844ce3a1
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153226
Reaction notes
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