Tert-Butanesulfinamide → HCID 87333909, compound

Reaction equation

[CH2:1]([S:4]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH2:2][CH3:3].[C:15]([S:19]([NH2:21])=[O:20])([CH3:18])([CH3:17])[CH3:16]>[O-]CC.[Ti+5].[O-]CC.[O-]CC.[O-]CC.[O-]CC.C1COCC1>[CH3:16][C:15]([S:19](/[N:21]=[CH:11]/[C:10]1[CH:13]=[CH:14][C:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[CH:8][CH:9]=1)=[O:20])([CH3:18])[CH3:17]

Participants

Procedure

4-(Propylsulphonyl)benzaldehyde (1.81 g, 8.53 mmol, prepared as described in Example 47a, tert-butyl sulphinamide (1.55 g, 12.8 mmol), titanium(V) ethoxide (3.58 mL, 17.1 mmol) and THF (50 mL) were heated at reflux for 3 h then stirred at room temperature overnight. The reaction mixture was quenched with water (200 mL) before addition of ethyl acetate (200 mL). Celite was added and the mixture stirred for 15 min before being filtered. The phases were separated and the organic extract dried (MgSO4) and concentrated. The yield of the title compound was assumed to be quantitative and the material was used without further purification. m/z (ES+) 316 (M+H).