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 219031Notes

Reaction equation

HRID 219031 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][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

Participants

7

Reactant 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

Product 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)-benzenesulfonamideYield 80.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-cyclohexyl-3-(hydroxymethyl)-N-({2-(trimethylsilyl)ethoxy}-methyl)benzenesulfonamide (508 mg) in DMF (8 ml) under nitrogen at 20° 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)+.

Workup

  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)

Sources & evidence

ORD record
ord-5d5928223e41441181603892d33a5bf1
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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