tert-Butylsulfinamide, (S)-(-)- → HCID 178455581, compound

HRID 1054465Notes

Reaction equation

HRID 1054465 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][C@H:15]1[CH2:19][CH2:18][O:17][CH2:16]1)=O.[CH3:20][C:21]([S@@:24]([NH2:26])=[O:25])([CH3:23])[CH3:22]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:1][CH2:2][CH2:3][CH2:4]/[C:5](=[N:26]/[S@:24]([C:21]([CH3:23])([CH3:22])[CH3:20])=[O:25])/[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][C@@H:15]1[CH2:19][CH2:18][O:17][CH2:16]1

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 118590572HCID 118590572, compound

Product 1

HCID 178455581HCID 178455581, compoundYield 296.7%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
27.5 °C

Procedure

Titanium (IV) ethoxide (17.5 g, 76.92 mmol) was added to a solution of (S)-4-chloro-1-(5-fluoro-2-((tetrahydrofuran-3-yl)oxy)phenyl)butan-1-one (11 g, 38.46 mmol) and (S)-2-methylpropane-2-sulfinamide (9.32 g, 76.92 mmol) in THF (170 mL) with stirring. The mixture was stirred continuously at 70° C. for 16 h. Reaction mixture was then cooled to a temperature of 20-35° C., quenched with saturated aqueous NH4Cl solution, diluted with ethyl acetate and filtered. The filtrate was washed with water followed by brine solution. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 44.5 g of the title compound as a colorless liquid. MS (ESI): 390.2 (M+H).

Workup

  1. stirringThe mixture was stirred continuously at 70° C. for 16 h
  2. customReaction mixture
  3. customquenched with saturated aqueous NH4Cl solution
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered
  6. washThe filtrate was washed with water
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-625a1b284ccc4a54ac1a336c2a788784
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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