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

HRID 916796Notes

Reaction equation

HRID 916796 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 ethyl acetate 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 ethyl acetate twice
  5. washThe solution was washed with brine twice
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-af9db90ef0be4ffe8e905b51bf8fb0c2
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

Loading…