Potassium trimethylsilanolate → (1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

HRID 2118324노트

반응식

HRID 2118324 반응식
[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:29][C@@H:28]([C:30]4[CH:41]=[CH:40][C:33]5[O:34][C:35]([CH3:39])([CH3:38])[O:36][CH2:37][C:32]=5[CH:31]=4)[O:27]C3=O)[CH:11]=[CH:12][CH:13]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>O1CCCC1>[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:29][C@@H:28]([C:30]3[CH:41]=[CH:40][C:33]4[O:34][C:35]([CH3:38])([CH3:39])[O:36][CH2:37][C:32]=4[CH:31]=3)[OH:27])[CH:11]=[CH:12][CH:13]=2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

4

반응물 2

HCID 23668039Potassium trimethylsilanolateHCID 69119380(5R)-3-(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

생성물 1

HCID 69119885(1R)-2-[(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)amino]-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol수율 82.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A stirred mixture of (5R)-3-(6-{4-[3-(cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.14 g) and potassium trimethyl silanolate (0.45 g) in tetrahydrofuran (10 ml) was heated to reflux for 2 h. The mixture was poured into phoshate buffer solution (pH 5, 50 ml) and extracted into ethyl acetate. The extracts were washed with water, dried (Na2SO4) and evaporated. The residual oil was purified on a biotage cartridge (8 g) using dichloromethane-ethanol-0.88 ammonia (100:8:1) as eluent. The appropriate fractions were evaporated to give the title compound (0.11 g) LCMS RT=2.89 min.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. extractionextracted into ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residual oil was purified on a biotage cartridge (8 g)
  8. customThe appropriate fractions were evaporated

출처 및 근거

ORD 기록
ord-dd5b4e1fab2245d59fce3eec26043ae6
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442839B2

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