Triethylamine → HCID 86673313, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].FC(F)(F)S(O[Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])(=O)=O.C(N(CC)CC)C.[C:31]([O:35][C:36](=[O:39])[CH2:37]Br)([CH3:34])([CH3:33])[CH3:32]>ClCCl>[C:31]([O:35][C:36](=[O:39])[CH2:37][NH:1][CH2:2][CH2:3][CH2:4][O:5][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])([CH3:34])([CH3:33])[CH3:32]Participants
Procedure
To a solution of 3-amino-1-propanol (2.0 mL, 26 mmol) in dichloromethane (20 mL) was added triisopropylsilyl trifluoromethanesulfonate (7.2 mL, 27 mmol), and the mixture was stirred at room temperature for 1 hour. Triethylamine (3.7 mL, 26 mmol) and bromoacetic acid tert-butyl ester (3.1 mL, 21 mmol) were added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (dichloromethane/methanol=97/3) to give the title compound (1.85 g, 5.4 mmol, 25%).
Workup
- stirringthe mixture was further stirred at room temperature for 1 hour
- washwashed with saturated aqueous sodium hydrogen carbonate
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol=97/3)
Sources & evidence
- ORD record
- ord-33af49072c2446b49d9f72ef5b9e91e7
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609715B2
Reaction notes
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