HCID 57907608, compound → HCID 57907594, compound

HRID 887085Notes

Reaction equation

HRID 887085 reaction equation
[Si:1]([O:8][CH:9]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)/[CH:10]=[N:11]/[S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:25]([Mg]Cl)=[CH2:26]>C1COCC1>[Si:1]([O:8][CH:9]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH:10]([NH:11][S:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH:25]=[CH2:26])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 57907608HCID 57907608, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 57907594HCID 57907594, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.4 g (6.20 mmol) of N-[(1E)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-chlorophenyl)ethylidene]-2-methylpropane-2-sulfinamide in 20 mL anhydrous THF cooled to 0° C. under nitrogen atmosphere (from Step D) was added a 1.6 M solution of vinyl magnesium chloride in THF (3.90 mL, 6.2 mmol) via syringe and the resulting mixture stirred for 1 h. The mixture was allowed to warm to room temperate and stirred for an additional hour. The reaction was quenched with saturated solution of ammonium chloride and extract with ethyl acetate. Combine organics, dry over 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 0-35% ethyl acetate in hexane to afford all four diastereomers as single isomers.

Workup

  1. temperatureto warm to room temperate
  2. stirringstirred for an additional hour
  3. customThe reaction was quenched with saturated solution of ammonium chloride
  4. extractionextract with ethyl acetate
  5. dry with materialCombine organics, dry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customThe residue was purified by Horizon MPLC, with a 40M+ silica gel column
  9. washeluting with a gradient eluent system of 0-35% ethyl acetate in hexane
  10. customto afford all four diastereomers as single isomers

Sources & evidence

ORD record
ord-a4e2e6aa0a5e4bfb81bd942557fa599a
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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