Hydrochloric Acid → HCID 131735840, compound

HRID 2206190Notes

Reaction equation

HRID 2206190 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([B:17]([OH:19])[OH:18])=[CH:13][CH:12]=1.Cl>CN(C=O)C>[O:6]=[C:2]1[N:3]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([B:17]([OH:19])[OH:18])=[CH:13][CH:12]=2)[CH2:4][CH2:5][O:1]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 27355934-(Bromomethyl)phenylboronic acid

Product 1

HCID 131735840HCID 131735840, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of oxazolidin-2-one (243 mg) in anhydrous DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 140 mg) in small portions under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, to the reaction mixture was added (4-(bromomethyl)phenyl)boronic acid (500 mg), and the mixture was stirred for 60 hr. To the reaction mixture was added ice water, and the aqueous layer was neutralized with 1N hydrochloric acid under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether and ethyl acetate to give the title compound (273 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 60 hr
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with diisopropyl ether and ethyl acetate

Sources & evidence

ORD record
ord-e37e975252d2424ea7952aeb555efa3e
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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