(Diethylamino)sulfur trifluoride → HCID 10202473, compound
Reaction equation
O[C:2]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].CCN(S(F)(F)[F:34])CC>C(Cl)Cl>[F:34][C:2]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Into a 50 mL 3 neck flask fitted with a stirrer and thermometer, [2-hydroxy-2-(4-{2-[(methylsulfonyl)amino]ethoxy}phenyl)cyclopentyl][(methylethyl)sulfonyl]amine (150 mg, 0.36 mmol) in CH2Cl2 (5 mL) is added dropwise to 0.01 mL DAST in CH2CL2 (15 mL) while stirring at −78° C. under a nitrogen atmosphere. The reaction is allowed to warm to room temperature and diluted with CH2Cl2 (20 mL). This organic layer is washed with H2O, dried over Na2SO4, filtered, and concentrated under reduced vacuum to yield the product. This material is purified via silica gel chromatography employing the Chromatotron® and using 2000 micron rotor while eluting with a suitable eluent, such as hexanes/ethyl acetate to provide the final title compound.
Workup
- temperatureto warm to room temperature
- washThis organic layer is washed with H2O
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced vacuum
- customto yield the product
- customThis material is purified via silica gel chromatography
- washwhile eluting with a suitable eluent, such as hexanes/ethyl acetate
Sources & evidence
- ORD record
- ord-e02f6f47f9864fe1a1d735eeee2fd6e4
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900353B2
Reaction notes
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