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 901597Notes

Reaction equation

HRID 901597 reaction equation
[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

Participants

6

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 468348293-(Hydroxymethyl)-N,N-bis{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

Product 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}benzenesulfonamideYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-4907641abf62424ab1854d3e3cd5290f
Source dataset
uspto-grants-2008_04
Patent number
US07361787B2

Reaction notes

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