Triethylamine → 2-(2-Bromo-phenyl)-N-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-acetamide
Reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH2:14])[CH2:4][O:3]1.C(N(CC)CC)C.[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31](Cl)=[O:32]>ClCCl>[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([NH:14][C@H:5]1[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][C@H:6]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 250 mg (1.2 mmol) of (4S,5S)-amine 1 in dichloromethane (3 mL) was added 0.16 mL (1.2 mmol) of triethylamine followed by dropwise addition of 0.17 mL (1.2 mmol) of 2-bromophenylacetyl chloride. After stirring for ˜96 h at 25° C., the reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (hexanes/ethyl acetate) to yield 290 mg (60%) of the title compound.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by column chromatography (hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-39e8bfadf0f3480eb724d36ebe0fa081
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06951882B2
Reaction notes
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