Dimethyl Sulfide → N-(4-methoxybenzyl)-2-(methoxymethyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide
반응식
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][C:19](=O)[CH:18]([CH2:22][O:23][CH3:24])[O:17][C:16]=3[CH:25]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CSC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([C:26]2[S:27][CH:28]=[CH:29][N:30]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH:18]([CH2:22][O:23][CH3:24])[O:17][C:16]=3[CH:25]=2)(=[O:11])=[O:10])=[CH:31][CH:32]=1참가 물질
4
반응물 2
생성물 1
시약·촉매·용매 1
실험 절차
To a solution of N-(4-methoxybenzyl)-2-(methoxymethyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (500 mg, 1.05 mmol) in THF (10 mL) was added BH3.DMS (0.15 mL, 1.57 mmol, Aldrich) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h. After completion, the reaction mixture was quenched with methanol (7 mL) and was azeotroped with methanol (3×15 mL). The solvent was removed under reduced pressure and the crude material thus obtained was purified by column chromatography (silica: 100-200; elution: 30% ethyl acetate in hexane) to get pure N-(4-methoxybenzyl)-2-(methoxymethyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (350 mg, 71.6%) as a brown solid. m/z (ESI) 462.2 (M+H)+.