Phosphate → (5R)-3-[6-(2-{[3-(Dimethylamino)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 503082Notes

Reaction equation

HRID 503082 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[H-].[Na+].CS(O[CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][C@@H:31]([C:33]2[CH:44]=[CH:43][C:36]3[O:37][C:38]([CH3:42])([CH3:41])[O:39][CH2:40][C:35]=3[CH:34]=2)[O:30][C:29]1=[O:45])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][O:7][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:32][C@@H:31]([C:33]2[CH:44]=[CH:43][C:36]3[O:37][C:38]([CH3:41])([CH3:42])[O:39][CH2:40][C:35]=3[CH:34]=2)[O:30][C:29]1=[O:45]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 90133m-(Dimethylamino)benzyl alcoholHCID 468322282-({6-[(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate

Product 1

HCID 66845431(5R)-3-[6-(2-{[3-(Dimethylamino)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-dimethylaminobenzyl alcohol (641 mg) in DMF (3 ml) under nitrogen was treated with sodium hydride (220 mg, 60% in oil) and the mixture stirred at 20° for 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 (2.00 g) in DMF (5 ml) was added and the mixture was stirred at 20° for 21 h. Phosphate buffer solution (15 ml, pH6.5) was added, the mixture stirred for 15 min and then extracted with EtOAc. The combined organic layers were washed with water, dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by Biotage (40 g). Elution with EtOAc-PE (1:2) gave the title compound (2.125 g). LCMS RT=3.47 min.

Workup

  1. stirringthe mixture was stirred at 20° for 21 h
  2. stirringthe mixture stirred for 15 min
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by Biotage (40 g)
  8. washElution with EtOAc-PE (1:2)

Sources & evidence

ORD record
ord-188e32319c374f3ab58a4cb48fe96801
Source dataset
uspto-grants-2010_08
Patent number
US07776895B2

Reaction notes

Loading…