Potassium trimethylsilanolate → (1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 219007노트

반응식

HRID 219007 반응식
[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][C@@H:18]([C:20]2[CH:31]=[CH:30][C:23]3[O:24][C:25]([CH3:29])([CH3:28])[O:26][CH2:27][C:22]=3[CH:21]=2)[O:17]C1=O.C[Si](C)(C)[O-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:19][C@@H:18]([C:20]1[CH:31]=[CH:30][C:23]2[O:24][C:25]([CH3:28])([CH3:29])[O:26][CH2:27][C:22]=2[CH:21]=1)[OH:17]

참가 물질

4

반응물 2

HCID 23668039Potassium trimethylsilanolateHCID 46833391(5R)-3-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

생성물 1

HCID 46834265(1R)-2-(6-(2-((2,6-dichlorophenyl)methoxy)ethoxy)hexylamino)-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol수율 97.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (5R)-3-(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (140 mg) in THF (7 ml) under nitrogen was treated with potassium trimethylsilanolate (130 mg) and the mixture was heated (oil bath temperature 80°) with stirring for 3 h. The mixture was cooled to 20° and was partitioned between phosphate buffer solution (20 ml, pH6.5) and EtOAc (20 ml). The organic phase was separated, dried (NaSO4) and the solvent evaporated in vacuo to give the title compound (130 mg). LCMS RT=3.00 min.

후처리

  1. temperaturethe mixture was heated (oil bath temperature 80°)
  2. temperatureThe mixture was cooled to 20°
  3. customwas partitioned between phosphate buffer solution (20 ml, pH6.5) and EtOAc (20 ml)
  4. customThe organic phase was separated
  5. dry with materialdried (NaSO4)
  6. customthe solvent evaporated in vacuo

출처 및 근거

ORD 기록
ord-0d2e34ff89e045c886846ccf664896a0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198483B2

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