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

HRID 2118324ノート

反応式

HRID 2118324 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dd5b4e1fab2245d59fce3eec26043ae6
出典データセット
uspto-grants-2008_10
特許番号
US07442839B2

反応ノート

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