Triethylamine → (trans)-3-[3-(4-Bromo-phenyl)-acryloyl]-4-methyl-5-phenyl-oxazolidin-2-one

HRID 1294365Notes

Reaction equation

HRID 1294365 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2C[C@H:9]2[C:11]([O:13]CC)=O)=[CH:4][CH:3]=1.[CH3:16][C@@H:17]1[C@H:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:20][C:19](=[O:28])[NH:18]1.CCN(CC)CC>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:11]([N:18]2[C@@H:17]([CH3:16])[C@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:20][C:19]2=[O:28])=[O:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 66578655ethyl (1R,2R)-2-(4-bromophenyl)cyclopropanecarboxylate

Product 1

HCID 69159075(trans)-3-[3-(4-Bromo-phenyl)-acryloyl]-4-methyl-5-phenyl-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-bromo-phenyl)-1-imidazol-1-yl-propenone (1.05 eq) from Step 1, (4R, 5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone (1.0 eq) or (−)-isomer and Et3N (1.2 eq) in CH3CN (0.2M) was refluxed overnight. The resulting mixture was cooled to rt, filtered on a pad of silica gel and concentrated. Crystallization in hexane:Et2O afforded the title compound as a white solid.

Workup

  1. filtrationfiltered on a pad of silica gel
  2. concentrationconcentrated
  3. customCrystallization in hexane

Sources & evidence

ORD record
ord-43b4de3727ac4a31b776e4909e9ef10d
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

Loading…