Water → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{2-[4-(2-hydroxyethoxy)phenyl]ethyl}-1,3-oxazolidin-2-one

HRID 916798Notes

Reaction equation

HRID 916798 reaction equation
C([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[CH2:20][C@@H:19]([C:21]3[CH:32]=[CH:31][C:24]4[O:25][C:26]([CH3:30])([CH3:29])[O:27][CH2:28][C:23]=4[CH:22]=3)[O:18][C:17]2=[O:33])=[CH:10][CH:9]=1)(=O)C.O([Si](C)(C)C)[K].P([O-])([O-])([O-])=O.O>C1COCC1>[CH3:29][C:26]1([CH3:30])[O:25][C:24]2[CH:31]=[CH:32][C:21]([C@H:19]3[O:18][C:17](=[O:33])[N:16]([CH2:15][CH2:14][C:11]4[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][OH:4])=[CH:13][CH:12]=4)[CH2:20]3)=[CH:22][C:23]=2[CH2:28][O:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 1061PhosphateHCID 693917962-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl acetateHCID 178504318HCID 178504318, compound

Product 1

HCID 11441342(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{2-[4-(2-hydroxyethoxy)phenyl]ethyl}-1,3-oxazolidin-2-oneYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl acetate (3.7 g) in THF (100 mL) was treated with KOSiMe3 (1.39 g) and stirred at room temperature for 3 h. The solution was then poured into phosphate buffer (pH 6.5) and water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (3.31 g). LCMS RT=2.91 min.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1126df710d84c5a9da3a9728d7d0b6c
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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