Tetrabutylammonium Fluoride → (s)-Di-tert-butyl 4-(3-(2,3-difluorobenzyl)-1-methylureido)-5-hydroxypentyl phosphate
反応式
[P:1]([O:13][CH2:14][CH2:15][CH2:16][C@H:17]([N:27]([CH3:40])[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=1[F:39])=[O:29])[CH2:18][O:19][Si](C(C)(C)C)(C)C)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[P:1]([O:13][CH2:14][CH2:15][CH2:16][C@H:17]([N:27]([CH3:40])[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=1[F:39])=[O:29])[CH2:18][OH:19])([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of (S)-di-tert-butyl 5-(tert-butyldimethylsilyloxy)-4-(3-(2,3-difluorobenzyl)-1-methylureido)pentyl phosphate (4.1 g, 7.95 mmol) in THF (40 mL) was added TBAF (1.0 M in THF, 8.0 mL, 8.0 mmol). The resulting solution was stirred at RT for 1 h. The mixture was quenched with sat. NH4Cl and diluted with EtOAc. The organic layer was washed with sat. NH4Cl (×2) and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-di-tert-butyl 4-(3-(2,3-difluorobenzyl)-1-methylureido)-5-hydroxypentyl phosphate (2.52 g, 61%) as a colorless oil. LRMS (M+H+−2 tBu) m/z 383.0.