Sodium bis(2-methoxyethoxy)aluminiumhydride → N-{4-[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-2-hydroxyphenyl}acetamide
반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17](OC(C)(C)C)=[O:18])=[C:15]([NH2:24])[N:14]=[C:13]([C:25]3[C:30]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)=[CH:29][CH:28]=[CH:27][C:26]=3[O:41][CH2:42][CH:43]3[CH2:45][CH2:44]3)[CH:12]=2)=[CH:7][C:6]=1[OH:46])(=[O:3])[CH3:2].[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1COCC1>[NH2:24][C:15]1[C:16]([CH2:17][OH:18])=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([OH:46])[CH:7]=2)[CH:12]=[C:13]([C:25]2[C:30]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)=[CH:29][CH:28]=[CH:27][C:26]=2[O:41][CH2:42][CH:43]2[CH2:45][CH2:44]2)[N:14]=1참가 물질
4
실험 절차
To a cold (0° C.) solution of tert-butyl 4-[4-(acetylamino)-3-hydroxyphenyl]-2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}nicotinate (1.65 g, 2.64 mmol) in THF (25.0 mL) under argon atmosphere was added a solution of sodium bis(2-methoxyethoxy)aluminum hydride (3.7 N in toluene, 4.12 mL, 21.1 mmol) in THF (3 mL) dropwise. After being stirred for 30 minutes, the mixture was quenched with ethyl acetate and poured into saturated aqueous sodium potassium tartarate. The extracted organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol, 19:1-9:1) to give N-{4-[2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-3-(hydroxymethyl)-4-pyridinyl]-2-hydroxyphenyl}acetamide (0.48 g, 33%); LC-MS (m/z=556, M+1).