Triethylamine → HCID 86622980, compound
Reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:9]([CH2:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[F:20])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[CH2:21]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]([CH2:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[F:20])[CH:10]=[O:11])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 1.5 °C
Procedure
To a solution of (R)-2-Dibenzylamino-3-(2,5-difluoro-phenyl)-propan-1-ol (5.10 g, 13.9 mmol) in DMSO (1 mL) and Triethylamine (7.83 mL, 56.2 mmol) at −9° C. is added a solution of Sulfur Trioxide Pyridine Complex (4.43 g, 27.3 mmol) in DMSO (19.6 mL) over a period of 60 min, the reaction temperature is maintained below 4° C. The reaction is allowed to stir an additional 15 min at 0-3° C. after which the reaction is quenched by addition of water (50 mL) over a period of 60 min, the reaction temperature is maintained below 10° C. The product is extracted into MTBE, the organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide the title compound.
Workup
- temperaturethe reaction temperature is maintained below 4° C
- customis quenched by addition of water (50 mL) over a period of 60 min
- temperaturethe reaction temperature is maintained below 10° C
- extractionThe product is extracted into MTBE
- dry with materialthe organic phase is dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3dfd89b5fc484fd788e4bc379da4229f
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133907B2
Reaction notes
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