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

HRID 916076노트

반응식

HRID 916076 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f91081b6cd8e48b587cfde224a8a2f22
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268147B2

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