Tert-Butanesulfinamide → HCID 57907608, compound

HRID 403437Notes

Reaction equation

HRID 403437 reaction equation
[Si:1]([O:8][CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:19][C:20]([S:23]([NH2:25])=[O:24])([CH3:22])[CH3:21]>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[Si:1]([O:8][CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)/[CH:10]=[N:25]/[S:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 18794325HCID 18794325, compound

Product 1

HCID 57907608HCID 57907608, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.0 g (10.6 mmol) of {[tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)acetaldehyde (from Step C) and 1.3 g (10.6 mmol) of (R or S)-2-methyl-2-propanesulfinamide in 50 mL anhydrous dichloromethane was added copper(II) sulfate (3.4 g, 21.2 mmol) and the resulting mixture was stirred at room temperature under nitrogen atmosphere for 16 h. Wash reaction with water and extract with dichloromethane. Dry the organics with magnesium sulfate, filter and concentrate under vacuum. The residue was purified by Horizon MPLC, with a 40M+ silica gel column, eluting with a gradient eluent system of 0-25% ethyl acetate in hexane to afford the title compound (3.26 g, 80%). %). m/z (ES) 387, 390 (M, M+2)+.

Workup

  1. washWash
  2. customreaction with water
  3. extractionextract with dichloromethane
  4. dry with materialDry the organics with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under vacuum
  7. customThe residue was purified by Horizon MPLC, with a 40M+ silica gel column
  8. washeluting with a gradient eluent system of 0-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-321a21a761314eafb718079f2f9f24bc
Source dataset
uspto-grants-2014_06
Patent number
US08748433B2

Reaction notes

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