Hexachloroethane → HCID 53414093, compound

A solution of triphenylphosphine (65.8 g, 0.251 mol)) and hexachloroethane (59.4 g, 0.251 mol) in dichloromethane (850 mL) was added in one portion to a solution of N-Boc-serine methyl ester (50 g, 0.228 mol) in dichloromethane (170 mL) under argon atmosphere. The reaction mixture was stirred at room temperature for 2 h and then the reaction was quenched with a saturated solution of NaHCO3 (150 mL). The organic product was extracted with dichloromethane (2×300 mL) and the combined organic layers was washed with brine (300 mL) and dried over anhydrous sodium sulphate. The solution was concentrated under reduced pressure and then triturated with Et2O (500 mL). After filtration and evaporation of the solvent, the crude product was purified by chromatography on a silica column eluted with 6-8% EtOAc in pet. ether) which gave the title compound (42 g, 78%).

1. customthe reaction was quenched with a saturated solution of NaHCO3 (150 mL)
2. extractionThe organic product was extracted with dichloromethane (2×300 mL)
3. washthe combined organic layers was washed with brine (300 mL)
4. dry with materialdried over anhydrous sodium sulphate
5. concentrationThe solution was concentrated under reduced pressure
6. customtriturated with Et2O (500 mL)
7. filtrationAfter filtration and evaporation of the solvent
8. customthe crude product was purified by chromatography on a silica column
9. washeluted with 6-8% EtOAc in pet. ether) which

ORD record

ord-49c26c084ded46e6a5d3a44bdc971ceb

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859505B2