Phosphate → N-Cyclohexyl-3-{[2-(4-[2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

HRID 916835노트

반응식

HRID 916835 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][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][N:45]2[CH2:49][C@@H:48]([C:50]3[CH:61]=[CH:60][C:53]4[O:54][C:55]([CH3:59])([CH3:58])[O:56][CH2:57][C:52]=4[CH:51]=3)[O:47][C:46]2=[O:62])=[CH:39][CH:38]=1)(=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][C:37]3[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][N:45]4[CH2:49][C@@H:48]([C:50]5[CH:61]=[CH:60][C:53]6[O:54][C:55]([CH3:58])([CH3:59])[O:56][CH2:57][C:52]=6[CH:51]=5)[O:47][C:46]4=[O:62])=[CH:39][CH:38]=3)[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 66845530N-Cyclohexyl-3-(hydroxymethyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamideHCID 866016632-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl methanesulfonate

생성물 1

HCID 69424487N-Cyclohexyl-3-{[2-(4-[2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethoxy]methyl}-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
20 °C

실험 절차

A solution of N-cyclohexyl-3-(hydroxymethyl)-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide (207 mg) in DMF (5 ml) under nitrogen was treated with sodium hydride (60% dispersion in mineral oil, 24 mg) and the mixture stirred at 20° C. for 15 min. A solution of 2-(4-{2-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl methanesulfonate [Example 15 i)] (170 mg) in DMF (3 ml) was added and the mixture stirred at 20° C. for 18 h. Phosphate buffer solution (pH 6.5, 15 ml) and water (15 ml) were added and the mixture was extracted with EtOAc. The combined extracts were washed with water and dried (Na2SO4). Solvent evaporation in vacuo gave a residue which was purified by “Flashmaster” chromatography on silica gel. Elution with EtOAc-cyclohexane (2:3) gave the title compound (125 mg). LCMS RT=4.35 min.

후처리

  1. stirringthe mixture stirred at 20° C. for 18 h
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customSolvent evaporation in vacuo
  6. customgave a residue which
  7. customwas purified by “Flashmaster” chromatography on silica gel
  8. washElution with EtOAc-cyclohexane (2:3)

출처 및 근거

ORD 기록
ord-19717d1cd7ad41f7bdb9bae44e59dd09
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271197B2

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