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

HRID 2116993Notes

Reaction equation

HRID 2116993 reaction equation
[CH:1]1([S:6][C:7]2[CH:8]=[C:9]([CH2:13][OH:14])[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CS(O[CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:35][C@@H:34]([C:36]2[CH:47]=[CH:46][C:39]3[O:40][C:41]([CH3:45])([CH3:44])[O:42][CH2:43][C:38]=3[CH:37]=2)[O:33][C:32]1=[O:48])(=O)=O.P([O-])([O-])([O-])=O>CN(C=O)C>[CH:1]1([S:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[CH2:13][O:14][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31]2[CH2:35][C@@H:34]([C:36]3[CH:47]=[CH:46][C:39]4[O:40][C:41]([CH3:44])([CH3:45])[O:42][CH2:43][C:38]=4[CH:37]=3)[O:33][C:32]2=[O:48])[CH2:5][CH2:4][CH2:3][CH2:2]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 66347770[3-(Cyclopentylsulfanyl)phenyl]methanol

Product 1

HCID 66845210(5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 46.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of [3-(cyclopentylthio)phenyl]methanol (270 mg) in dry DMF (10 ml) under nitrogen was treated with sodium hydride (60% dispersion on mineral oil, 57 mg) and the mixture stirred for 1 h. 2-({6-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]hexyl}oxy)ethyl methanesulfonate (0.4 g) in dry DMF (2 ml) was then added and the mixture stirred for 18 h. Phosphate buffer solution (pH6.5) was added and the mixture extracted with ethyl acetate. The combined extracts were washed with water and dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with 10% to 20% ethyl acetate-cyclohexane to give the title compound (0.23 g). LCMS RT=4.08 min.

Workup

  1. stirringthe mixture stirred for 18 h
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with 10% to 20% ethyl acetate-cyclohexane

Sources & evidence

ORD record
ord-d10890b868e248029cd307cd88ea1d45
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

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