Phosphate → N-Cyclohexyl-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-({2-(trimethylsilyl)ethoxy}methyl)-benzenesulfonamide

HRID 503072노트

반응식

HRID 503072 반응식
[CH:1]1([N:7]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=2)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CS(O[CH2:34][CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N:43]1[CH2:47][C@@H:46]([C:48]2[CH:59]=[CH:58][C:51]3[O:52][C:53]([CH3:57])([CH3:56])[O:54][CH2:55][C:50]=3[CH:49]=2)[O:45][C:44]1=[O:60])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C.O>[CH:1]1([N:7]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][CH2:34][CH2:35][O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N:43]3[CH2:47][C@@H:46]([C:48]4[CH:59]=[CH:58][C:51]5[O:52][C:53]([CH3:56])([CH3:57])[O:54][CH2:55][C:50]=5[CH:49]=4)[O:45][C:44]3=[O:60])[CH:12]=2)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

7

반응물 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 66845530N-Cyclohexyl-3-(hydroxymethyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

생성물 1

HCID 66845045N-Cyclohexyl-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-({2-(trimethylsilyl)ethoxy}methyl)-benzenesulfonamide수율 80.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

A solution of N-cyclohexyl-3-(hydroxymethyl)-N-({2-(trimethylsilyl)ethoxy}-methyl)benzenesulfonamide (508 mg) in DMF (8 ml) under nitrogen at 200 was treated with sodium hydride (60% dispersion in mineral oil, 58 mg) and the mixture was stirred 15 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 (400 mg) in DMF (2 ml) was added and the mixture was stirred at 20° for 72 h. Phosphate buffer solution (pH 6.5, 10 ml) and water (20 ml) were added and the mixture was extracted with EtOAc (30 ml). The extract was washed with water (2×30 ml), dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by flash chromatography on silica gel. Elution with EtOAc-PE (1:1) gave the title compound (530 mg). LCMS RT=4.47 min, ES+ve 793 (MH)+.

후처리

  1. stirringthe mixture was stirred at 20° for 72 h
  2. extractionthe mixture was extracted with EtOAc (30 ml)
  3. washThe extract was washed with water (2×30 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel
  7. washElution with EtOAc-PE (1:1)

출처 및 근거

ORD 기록
ord-466fbeb55bfa4e32a423233a22af86d4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776895B2

반응 노트

불러오는 중…