Acat-IN-2 → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(2-hydroxy-ethylamino)-2,6-diisopropyl-phenyl ester
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([O:11][S:12](=[O:33])(=[O:32])[NH:13][C:14](=[O:31])[CH2:15][C:16]2[C:21]([CH:22]([CH3:24])[CH3:23])=[CH:20][C:19]([CH:25]([CH3:27])[CH3:26])=[CH:18][C:17]=2[CH:28]([CH3:30])[CH3:29])=[C:4]([CH:34]([CH3:36])[CH3:35])[CH:3]=1.[C:37](O)(=[O:39])[CH3:38].O>>[OH:39][CH2:37][CH2:38][NH:1][C:2]1[CH:3]=[C:4]([CH:34]([CH3:36])[CH3:35])[C:5]([O:11][S:12](=[O:33])(=[O:32])[NH:13][C:14](=[O:31])[CH2:15][C:16]2[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:18][C:19]([CH:25]([CH3:26])[CH3:27])=[CH:20][C:21]=2[CH:22]([CH3:23])[CH3:24])=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:7]=1Participants
3
Procedure
[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-amino-2,6-diisopropyl-phenyl ester (1.0 g, 1.9 mmol) was suspended in 50 mL of 1:1 glacial acetic acid/water and a stream of ethylene oxide was bubbled in for 15 minutes. The reaction mixture was sealed and allowed to stir overnight. The reaction mixture was concentrated in vacuo and partitioned between saturated aqueous sodium bicarbonate and dichloromethane. Dried the organic layer over magnesium sulfate, filtered, and concentrated to give an oily solid. Chromatography on silica gel (20% ethyl acetate/hexanes) gave 0.07 g of the title compound as a tan solid; mp 149-152° C.