HCID 57907608, compound → HCID 57907594, compound

HRID 243649Notes

Reaction equation

HRID 243649 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-38afe2a0196046a58c468bdb4da2b1ea
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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