Benzylethanolamine → HCID 66614863, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[CH2:9]I)=[CH:4][C:3]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].[CH2:24]([NH:31][CH2:32][CH2:33][OH:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([N:31]([CH2:32][CH2:33][OH:34])[CH2:9][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:4]=1)[O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
(R)—N-(2-Fluoro-5-(2-iodo-1-(triethylsilyloxy)ethyl)phenyl)methanesulfonamide (500 mg) and 2-(benzylamino)ethanol (1.6 g) were admixed with each other and stirred overnight at 100° C. After cooling to room temperature, the reaction solution was purified by column chromatography (“COLUMN-H”; n-hexane:ethyl acetate=2:1) to obtain (R)—N-(5-(2-(benzyl(2-hydroxyethyl)amino)-1-(triethylsilyloxy)ethyl)-2-fluorophenyl)methanesulfonamide (477.5 mg), which was then added with 4-N,N-dimethylaminopyridine (12 mg), triethylamine (163 μL), and THF (15 mL), and then Boc2O-THF solution [10 mL; solution prepared by dissolving Boc2O (230 mg) in THF (10 mL)] was added dropwise thereto. The mixture was stirred at room temperature for 3 hours. After concentrating the reaction solution under reduced pressure, the residue was purified by column chromatography (“COLUMN-H”; n-hexane:ethyl acetate=3:1) to obtain the title compound (500.3 mg).
Workup
- temperatureAfter cooling to room temperature
- customthe reaction solution was purified by column chromatography (“COLUMN-H”; n-hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-b4d519191fbf42deb73b082849a60191
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304443B2
Reaction notes
Loading…