Phosphate → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-{[2-(trimethylsilyl)ethoxy]methoxy}benzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one

HRID 916810Notes

Reaction equation

HRID 916810 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1.[H-].[Na+].CS(O[CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][N:36]2[CH2:40][C@@H:39]([C:41]3[CH:52]=[CH:51][C:44]4[O:45][C:46]([CH3:50])([CH3:49])[O:47][CH2:48][C:43]=4[CH:42]=3)[O:38][C:37]2=[O:53])=[CH:30][CH:29]=1)(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH3:49][C:46]1([CH3:50])[O:45][C:44]2[CH:51]=[CH:52][C:41]([C@H:39]3[O:38][C:37](=[O:53])[N:36]([CH2:35][CH2:34][C:31]4[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][O:15][CH2:14][C:10]5[CH:11]=[CH:12][CH:13]=[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:17])([CH3:16])[CH3:1])[CH:9]=5)=[CH:33][CH:32]=4)[CH2:40]3)=[CH:42][C:43]=2[CH2:48][O:47]1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 22127149(3-{[2-(Trimethylsilyl)ethoxy]methoxy}phenyl)methanolHCID 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 69388447(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(3-{[2-(trimethylsilyl)ethoxy]methoxy}benzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (3-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)methanol in DMF (5 ml) under nitrogen was treated with sodium hydride (18 mg, 60% in oil) and the mixture was stirred at 20° C. for 15 min. 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 (150 mg) was added and the mixture was stirred at 20° C. for 20 h. Phosphate buffer solution (20 ml, pH6.5) was added and the mixture was extracted with EtOAc (30 ml). The organic extract was washed with water (2×20 ml) and dried (Na2SO4). The solvent was evaporated in vacuo to give a residue which was purified by chromatography on flash silica gel. Elution with EtOAc-petroleum ether 40°-60° (1:1) gave the title compound (90 mg) LCMS RT=4.07 min.

Workup

  1. stirringthe mixture was stirred at 20° C. for 20 h
  2. extractionthe mixture was extracted with EtOAc (30 ml)
  3. extractionThe organic extract
  4. washwas washed with water (2×20 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated in vacuo
  7. customto give a residue which
  8. customwas purified by chromatography on flash silica gel
  9. washElution with EtOAc-petroleum ether 40°-60° (1:1)

Sources & evidence

ORD record
ord-17002fac826b4a1baa7e9471999fe97b
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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