HCID 86663862, compound → HCID 66975410, compound

HRID 1022660Notes

Reaction equation

HRID 1022660 reaction equation
[CH2:1]([N:8]([CH2:22][CH2:23][OH:24])[C:9]([CH:11]1[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH2:1]([N:8]1[C:9](=[O:10])[CH:11]([OH:12])[CH:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[O:24][CH2:23][CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86663862HCID 86663862, compound

Product 1

HCID 66975410HCID 66975410, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2RS,3SR)—N-benzyl-3-(3,4-dichlorophenyl)-N-(2-hydroxyethyl)oxirane-2-carboxamide (42.2 g) in acetonitrile (350 ml) was added scandium(III)trifluoromethanesulfonate (5.67 g), and the mixture was stirred at room temperature for 20 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (31.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b3be6266813e43bd968deac698b13446
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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