(Diethylamino)sulfur trifluoride → HCID 86677912, compound
Reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH3:13])[C:9](O)([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:21])CC>ClCCl>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH3:13])[C:9]([F:21])([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -76 °C
Procedure
In a dry round-bottomed flask, ((R)-2-hydroxy-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester (534 mg, 2.36 mmol) was dissolved in dichloromethane (22 ml). The solution was cooled to −76° C. and DAST (0.34 ml, 2.57 mmol) was added dropwise. The reaction mixture was stirred at −76° C. for 1.5 h then quenched with saturated aqueous NaHCO3 (5 mL), warmed to room temperature and extracted with dichloromethane (2×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to afford 534 mg of ((R)-2-fluoro-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester as a yellow oil which was used without further purification.
Workup
- customthen quenched with saturated aqueous NaHCO3 (5 mL)
- temperaturewarmed to room temperature
- extractionextracted with dichloromethane (2×)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6f0725f44f774cbb8cda575e4fdf18da
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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