Hydrochloric Acid → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 218991Notes

Reaction equation

HRID 218991 reaction equation
[CH3:1][C:2]1([CH3:23])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H:12](O)[CH2:13][NH:14][C:15](=[O:21])[O:16]C(C)(C)C)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].Cl>CN(C=O)C.O>[CH3:23][C:2]1([CH3:1])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:21])[NH:14][CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10881838Carbamic acid, [(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

tert-Butyl(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethylcarbamate, (86.37 g) in DMF (600 ml) was added dropwise to a stirred suspension of sodium hydride (60% oil dispersion, 11.9 g) in DMF (160 ml) with cooling such that the internal temperature remained at 0° under nitrogen. The mixture was stirred at 21° for 2 h. The mixture was recooled to 0° and 2M HCl (134 ml) was added. The mixture was diluted with water and the product was extracted with EtOAc twice. The solution was washed with brine twice, dried (MgSO4) and evaporated to give the title compound (63.55 g). LCMS RT=2.66 min.

Workup

  1. temperaturewith cooling such that the internal temperature
  2. customremained at 0° under nitrogen
  3. customwas recooled to 0°
  4. extractionthe product was extracted with EtOAc twice
  5. washThe solution was washed with brine twice
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-2528afd55aba44ed832607da0d4060a6
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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