Phosphate → 3-{[2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl}-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

HRID 219016ノート

反応式

HRID 219016 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].CS(O[CH2:36][CH2:37][O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][N:45]1[CH2:49][C@@H:48]([C:50]2[CH:61]=[CH:60][C:53]3[O:54][C:55]([CH3:59])([CH3:58])[O:56][CH2:57][C:52]=3[CH:51]=2)[O:47][C:46]1=[O:62])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH3:58][C:55]1([CH3:59])[O:54][C:53]2[CH:60]=[CH:61][C:50]([C@H:48]3[O:47][C:46](=[O:62])[N:45]([CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][O:1][CH2:2][C:3]4[CH:4]=[C:5]([S:9]([N:12]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:20])[CH3:18])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=4)[CH2:49]3)=[CH:51][C:52]=2[CH2:57][O:56]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 468348293-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

生成物 1

HCID 468339903-{[2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethoxy]methyl}-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide収率 63.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 3-(hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide (512 mg) in DMF (4 ml) under nitrogen was treated with sodium hydride (1.295 g, 60% in oil) and the mixture was stirred at 20° for 30 min. A solution of 2-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate (359 mg) in DMF (1 ml) was added and the mixture was stirred at 20° for 18 h. Phosphate buffer solution (25 ml, pH6.5) was added and the mixture was extracted with EtOAc. The extract was washed with water, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue. The residue was purified by chromatography on flash silica gel (30 mm diameter column). Elution with EtOAc-cyclohexane (2:3) then (1:1) gave the title compound (400 mg). LCMS RT=4.43 min.

後処理

  1. stirringthe mixture was stirred at 20° for 18 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe extract was washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customto give a residue
  7. customThe residue was purified by chromatography on flash silica gel (30 mm diameter column)
  8. washElution with EtOAc-cyclohexane (2:3)

出典と根拠

ORDレコード
ord-7293c3597b21416d81d0c5f179f31ebe
出典データセット
uspto-grants-2012_06
特許番号
US08198483B2

反応ノート

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