tert-Butylsulfinamide, (S)-(-)- → HCID 89618849, compound

HRID 926693Notes

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

Participants

Conditions

Temperature: 27.5 °C

Procedure

Titanium (IV) ethoxide (54.77 g, 240.13 mmol) was added to a solution of 4-chloro-1-(2,5-difluorophenyl)butan-1-one (35 g, 160.09 mmol) and (S)-2-methylpropane-2-sulfinamide (29.1 g, 240.13 mmol) in THF (400 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 ethylacetate 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 colourless liquid.

Workup

stirringThe mixture was stirred continuously at 70° C. for 16 h
customReaction mixture
customquenched with saturated aqueous NH4Cl solution
additiondiluted with ethylacetate
filtrationfiltered
washThe filtrate was washed with water
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d8d5b022042645259760a7ef3e0549d1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09289419B2

Reaction notes

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