Triethylamine → HCID 54374212, compound

HRID 387517Notes

Reaction equation

HRID 387517 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH2:12]([C@@H:19]1[CH2:23][O:22][C:21](=[O:24])[NH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>C1(C)C=CC=CC=1>[CH2:12]([C@@H:19]1[CH2:23][O:22][C:21](=[O:24])[N:20]1[C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 74654Benzeneacetic acid, 4-bromo-HCID 2734969(R)-4-Benzyl-2-oxazolidinone

Product 1

HCID 54374212HCID 54374212, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

2-(4-Bromophenyl)acetic acid (7.85 g, 36.5 mmol) and (R)-4-benzyloxazolidin-2-one (3.23 g, 18.3 mmol) were combined in toluene (30 mL) and triethylamine (10.2 mL, 73.0 mmol). The solution was then heated to 80° C., and a solution of pivaloyl chloride (4.49 mL, 36.5 mmol) in toluene (7.5 mL) was added slowly. The reaction was heated to 110° C. and stirred overnight. The reaction was then cooled, and the toluene solution was washed with 2N HCl, water, 5% Na2CO3, brine and then dried over Na3SO4. After removal of the solvent, the residue was purified by column chromatography to give (R)-4-benzyl-3-(2-(4-bromophenyl)acetyl)oxazolidin-2-one (5.65 g, 83%) as a solid.

Workup

  1. temperatureThe reaction was heated to 110° C.
  2. temperatureThe reaction was then cooled
  3. washthe toluene solution was washed with 2N HCl, water, 5% Na2CO3, brine
  4. dry with materialdried over Na3SO4
  5. customAfter removal of the solvent
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d3ade4ffde3849ab8e04cfb750c56c94
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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