Benzyl Bromide → HCID 57907391, compound

HRID 243697Notes

Reaction equation

HRID 243697 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]([OH:10])=[O:9])[CH2:5][CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:9])[CH2:5][CH2:4][O:3]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12676756(2-Oxo-1,3-oxazolidin-3-yl)acetic acid

Product 1

HCID 57907391HCID 57907391, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.0 g (6.9 mmol) of (2-oxo-1,3-oxazolidin-3-yl)acetic acid in 10 mL of anhydrous DMF was added 1.0 g (7.6 mmol) of potassium carbonate followed by 1.0 mL (8.3 mmol) of benzyl bromide. The reaction mixture was stirred for 3 h then quenched with water. The aqueous phase was extracted with ethyl acetate (3×25 mL) and the combined organics were washed with water (2×10 mL), brine (10 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by silica gel chromatography eluting with 50% ethyl acetate in hexanes to afford the title compound as a white solid 0.50 g (31%). LC-MS: m/z (ES) 236 (MH)+.

Workup

  1. customthen quenched with water
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×25 mL)
  3. washthe combined organics were washed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7bdd5bfd871740ee9a150cd87f1ce634
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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