tert-Butylsulfinamide, (S)-(-)- → (NE,S)-N-[(2-cyclopropylsulfanyl-5-nitrophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1515547Notes

Reaction equation

[CH:1]1([S:4][C:5]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=2[CH:7]=O)[CH2:3][CH2:2]1.[C:16]([S@@:20]([NH2:22])=[O:21])([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[CH:1]1([S:4][C:5]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:6]=2/[CH:7]=[N:22]/[S@:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:21])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 73 °C

Procedure

To 76A (2.02 g, 9.0 mmol), (S)-tert-butylsulfinamide (1.21 g, 10 mmol) in CH2Cl2 (40 mL) was added Ti(OEt)4 (10 mL, 45 mmol). The mixture was heated at 73° C. for 6.0 h. CH2Cl2 was removed under vacuo and the residue was suspended in EtOAc. To this suspension was added brine. The mixture was stirred at rt for 15 min before it was filtered through a pad of wet Celite®. The filtrate was extracted with EtOAc (3×50 mL). The organic layer was washed with brine and dried over Na2SO4. After removal of solvent, 85A (3.0 g, 100% yield) was obtained as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 0.72-0.81 (m, 2H) 1.21 (m, 2H) 1.28 (s, 9H) 2.14-2.21 (m, 1H) 7.89 (d, J=8.79 Hz, 1H) 8.24 (dd, J=8.79, 2.64 Hz, 1H) 8.60 (d, J=2.64 Hz, 1H) 8.77 (s, 1H).

Workup

customCH2Cl2 was removed under vacuo
additionTo this suspension was added brine
filtrationwas filtered through a pad of wet Celite®
extractionThe filtrate was extracted with EtOAc (3×50 mL)
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customAfter removal of solvent

Sources & evidence

ORD record: ord-39b799489835417cbe6282a32cf4d84a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222453B2

Reaction notes

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