Water → HCID 90022866, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:12][C:13](=[O:31])[CH2:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[C:20]([F:30])[CH:19]=1)=[O:16].O>C1COCC1>[F:30][C:20]1[CH:19]=[C:18]([NH:17][C:15](=[O:16])[CH2:14][C:13](=[O:31])[CH2:12][O:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH:23]=[CH:22][C:21]=1[N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1Participants
6
Procedure
To a solution of 3-fluorophenol (2.33 g, 20.8 mmol) in anhydrous THF (20 mL) was added NaH (909 mg, 22.7 mmol, 60%) and the mixture was stirred at rt for 3 h. A solution of 4-bromo-N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide (6.8 g, 18.9 mmol) in THF (40 mL) was added. The resulting mixture was stirred at rt overnight. The reaction mixture was then poured into 100 mL of water and the mixture was extracted with EtOAc (30 mL×5). The combined organic phases were washed with brine (50 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as a yellow solid (0.16 g, 2%).
Workup
- stirringThe resulting mixture was stirred at rt overnight
- extractionthe mixture was extracted with EtOAc (30 mL×5)
- washThe combined organic phases were washed with brine (50 mL×2)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)
Sources & evidence
- ORD record
- ord-8449c024cad64d188bb9f1be4ab5c53b
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
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