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 916835Notes

Reaction equation

HRID 916835 reaction equation
[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

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-19717d1cd7ad41f7bdb9bae44e59dd09
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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