Sodium hydride → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(4-isopropoxybenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-one

HRID 916823Notes

Reaction equation

HRID 916823 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[H-].[Na+].CS([O:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([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]([CH3:45])([CH3:44])[O:42][CH2:43][C:38]=4[CH:37]=3)[O:33][C:32]2=[O:48])=[CH:25][CH:24]=1)(=O)=O>CN(C=O)C.CCOC(C)=O>[CH3:44][C:41]1([CH3:45])[O:40][C:39]2[CH:46]=[CH:47][C:36]([C@H:34]3[O:33][C:32](=[O:48])[N:31]([CH2:30][CH2:29][C:26]4[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][O:19][CH2:11][C:8]5[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=5)=[CH:24][CH:25]=4)[CH2:35]3)=[CH:37][C:38]=2[CH2:43][O:42]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 250081(4-(Propan-2-yloxy)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 69390204(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-[2-(4-{2-[(4-isopropoxybenzyl)oxy]ethoxy}phenyl)ethyl]-1,3-oxazolidin-2-oneYield 49.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (4-isopropoxyphenyl)methanol (93 mg) in DMF (2 ml) was treated with sodium hydride (27 mg) under nitrogen and stirred for 0.5 h. To this was added the 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 (357 mg) {Example 15 i)} and the resulting solution was stirred for 18 h under nitrogen. The solution was then diluted in EtOAc, washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (Biotage, 40 g) eluting with 40-60° C. petroleum ether-EtOAc (2:1) to give the title compound (156 mg). LCMS RT=3.76 min.

Workup

  1. stirringthe resulting solution was stirred for 18 h under nitrogen
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (Biotage, 40 g)
  6. washeluting with 40-60° C. petroleum ether-EtOAc (2:1)

Sources & evidence

ORD record
ord-96b7e746a66a44089ecd70fe8e6d9354
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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