Phosphate → (5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 1014856ノート

反応式

HRID 1014856 の反応式
[CH:1]1([S:6][C:7]2[CH:8]=[C:9]([CH2:13][OH:14])[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CS(O[CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:35][C@@H:34]([C:36]2[CH:47]=[CH:46][C:39]3[O:40][C:41]([CH3:45])([CH3:44])[O:42][CH2:43][C:38]=3[CH:37]=2)[O:33][C:32]1=[O:48])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH:1]1([S:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[CH2:13][O:14][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]2[CH2:35][C@@H:34]([C:36]3[CH:47]=[CH:46][C:39]4[O:40][C:41]([CH3:44])([CH3:45])[O:42][CH2:43][C:38]=4[CH:37]=3)[O:33][C:32]2=[O:48])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 468322282-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonateHCID 66347770[3-(Cyclopentylsulfanyl)phenyl]methanol

生成物 1

HCID 66845210(5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one収率 46.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of [3-(cyclopentylthio)phenyl]methanol (270 mg) in dry DMF (10 ml) under nitrogen was treated with sodium hydride (60% dispersion on mineral oil, 57 mg) and the mixture stirred for 1 h. 2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate (0.4 g) in dry DMF (2 ml) was then added and the mixture stirred for 18 h. Phosphate buffer solution (pH6.5) was added and the mixture extracted with ethyl acetate. The combined extracts were washed with water and dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with 10% to 20% ethyl acetate-cyclohexane to give the title compound (0.23 g). LCMS RT=4.08 min.

後処理

  1. stirringthe mixture stirred for 18 h
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with 10% to 20% ethyl acetate-cyclohexane

出典と根拠

ORDレコード
ord-0558ad4341e64337aa93a77d93a64517
出典データセット
uspto-grants-2011_07
特許番号
US07982067B2

反応ノート

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