4-Methylbenzoyl Chloride → (S)-3-(p-methylbenzoyl)-4-methyl-2,5-oxazolidinedione

HRID 434128Notes

Reaction equation

HRID 434128 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[C:16](=[O:17])[O:15][C:14](=[O:18])[NH:13]1>C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]2[C@@H:12]([CH3:11])[C:16](=[O:17])[O:15][C:14]2=[O:18])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 10996998(S)-4-Methyloxazolidine-2,5-dione

Product 1

HCID 59119732(S)-3-(p-methylbenzoyl)-4-methyl-2,5-oxazolidinedioneYield 33%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

p-Methylbenzoyl chloride (309 mg, 2.0 mmol) was dissolved in ethyl acetate (5 mL), followed by the addition of (S)-4-methyl-2,5-oxazolidinedione (L-alanine-NCA) (230 mg, 2.0 mmol) under ice cooling. Further, a solution of 4-dimethylaminopyridine (244 mg, 2.0 mmol) in ethyl acetate (10 mL) was added dropwise under ice cooling over 20 minutes. After the resulting mixture was stirred as was at 0° C. for 2 hours, a precipitated salt was filtered off, and the filtrate was concentrated under reduced pressure. The concentration residue was re-dissolved in a mixed solvent consisting of ethyl acetate (5 mL) and hexane (5 mL), and insoluble matter was filtered off. The filtrate was concentrated under reduced pressure to afford the title compound (152 mg, 33%) as a colorless clear syrup.

Workup

  1. filtrationa precipitated salt was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe concentration residue was re-dissolved in a mixed solvent
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-22ab7094b1ab415382074e4e07bf8b9f
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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