Sodium Hydroxide → Methyl-(4-{(2r)-2-[(2r)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetate

HRID 916076ノート

反応式

HRID 916076 の反応式
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH2:14])[CH3:13])=[CH:7][CH:6]=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:31]Br)=[CH:26][C:25]=1[CH2:41][OH:42])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.[OH-].[Na+]>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:14][CH2:31][C@@H:30]([C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:25]([CH2:41][OH:42])[CH:26]=2)[O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH3:13])=[CH:7][CH:6]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanolHCID 58959790Methyl-{4-[(2r)-2-amino-propyl]phenyl}acetate

生成物 1

HCID 71168634Methyl-(4-{(2r)-2-[(2r)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetate収率 50.5%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Methyl-{4-[(2R)-2-amino-propyl]phenyl}acetate (Preparation 64) (7.00 g, 33.8 mmol), [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol (Preparation 39) (15.2 g, 33.8 mmol) and diisopropylethylamine (4.36 g, 33.8 mmol) were heated in dimethylsulfoxide (50 ml) at 90° C. under nitrogen for 16 hours. The mixture was cooled and diluted with ethyl acetate (250 ml) and basified with 1M aqueous sodium hydroxide. The aqueous was extracted with ethyl acetate (250 ml) and the combined organics washed with brine (3×200 ml) and dried (magnesium sulfate). The crude material was purified by chromatography (90:10 dichloromethane:methanol) to furnish an orange coloured oil (9.86 g).

後処理

  1. temperatureThe mixture was cooled
  2. extractionThe aqueous was extracted with ethyl acetate (250 ml)
  3. washthe combined organics washed with brine (3×200 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customThe crude material was purified by chromatography (90:10 dichloromethane:methanol)

出典と根拠

ORDレコード
ord-f91081b6cd8e48b587cfde224a8a2f22
出典データセット
uspto-grants-2007_09
特許番号
US07268147B2

反応ノート

読み込み中…