3-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester → 3-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester

HRID 1866511ノート

反応式

HRID 1866511 の反応式
[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14][CH2:15][C@@H:16]([C:25]2[CH:30]=[CH:29][C:28]([O:31]CC3C=CC=CC=3)=[C:27]([CH2:39][OH:40])[CH:26]=2)[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])([CH3:13])[CH3:12])[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14][CH2:15][C@H:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:39][OH:40])[CH:26]=2)([CH3:13])[CH3:12])[CH:5]=1

参加物

4

反応物 1

HCID 579782283-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester

生成物 1

HCID 690248003-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

3-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester (Preparation 35) (2.12 g, 3.70 mmol) and palladium-on-carbon (10%, 300 mg) in methanol (50 ml) were hydrogenated at room temperature and 60 psi for 18 hours. The reaction mixture was filtered through arbocel and the filtrate concentrated in vacuo, the residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume) to furnish the title compound, this material was taken up in diethylether and evaporated (×3) to yield a white foam (1.50 g).

後処理

  1. customwere hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered through arbocel
  3. concentrationthe filtrate concentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume)

出典と根拠

ORDレコード
ord-10f24f8a6028464fa839fe5c6d49600b
出典データセット
uspto-grants-2009_12
特許番号
US07629358B2

反応ノート

読み込み中…