Diethyl Carbonate → HCID 66818424, compound

HRID 1754939Notes

Reaction equation

HRID 1754939 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])=[CH:4][C:3]=1[CH3:14].[C:15](=O)(OCC)[O:16]CC.C[O-].[Na+].[NH4+].[Cl-]>O.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][C@H:10]([CH2:11][OH:12])[O:13][C:15]2=[O:16])=[CH:4][C:3]=1[CH3:14]

Participants

7

Reactant 4

HCID 7766Diethyl CarbonateHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 61143065HCID 61143065, compound

Product 1

HCID 66818424HCID 66818424, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (S)-3-(4-bromo-3-methyl-phenylamino)-propane-1,2-diol (202 mg, 0.777 mmol), diethyl carbonate (3 ml), sodium methoxide (28% in MeOH, 0.160 ml) and MeOH (4 ml) was stirred at 130° C. overnight. The reaction mixture was treated with saturated NH4Cl and H2O and extracted with AcOEt (×2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt) to give (R)-3-(4-bromo-3-methyl-phenyl)-5-hydroxymethyl-oxazolidin-2-one (170 mg, 77%).

Workup

  1. extractionextracted with AcOEt (×2)
  2. washsequentially washed with H2O and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt)

Sources & evidence

ORD record
ord-c554764b43004741b414bd0addc6b205
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…