Cesium carbonate → HCID 60030589, compound
Reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12].[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:28][C:29]1[N:30]=[CH:31][NH:32][CH:33]=1)[C:24]([O:26][CH3:27])=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C)C=O>[C:15]([O:19][C:20]([NH:22][C@@H:23]([CH2:28][C:29]1[N:30]=[CH:31][N:32]([CH2:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])[CH:33]=1)[C:24]([O:26][CH3:27])=[O:25])=[O:21])([CH3:18])([CH3:16])[CH3:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Cesium carbonate (1.95 g, 6 mmol) and 1-bromo-4,4,4-trifluorobutane (954 mg, 5 mmol) were added to a solution of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-imidazol-4-yl)propanoate (1.08 g, 4 mmol) in N,N-dimethylformamide (5 ml), and the reaction stirred at 70° C. for 3 hours. The cooled mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (150 ml) and water (50 ml). The layers were separated, the organic phase dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of cyclohexane:ethyl acetate (100:0 to 0:100) to afford the title compound as an oil, 840 mg, 55% yield.
Workup
- concentrationThe cooled mixture was concentrated under reduced pressure
- customthe residue partitioned between ethyl acetate (150 ml) and water (50 ml)
- customThe layers were separated
- dry with materialthe organic phase dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography on silica gel using an elution gradient of cyclohexane:ethyl acetate (100:0 to 0:100)
Sources & evidence
- ORD record
- ord-ff96d8c114f9406698548ef633072fec
- Source dataset
- uspto-grants-2005_09
- Patent number
- US06949577B2
Reaction notes
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