Benzoyl chloride → (S)-3-benzoyl-4-methyl-2,5-oxazolidinedione

HRID 434126Notes

Reaction equation

HRID 434126 reaction equation
CN1CCOCC1.[CH3:8][C@H:9]1[C:13](=[O:14])[O:12][C:11](=[O:15])[NH:10]1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:16]([N:10]1[C@@H:9]([CH3:8])[C:13](=[O:14])[O:12][C:11]1=[O:15])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 79724-MethylmorpholineHCID 10996998(S)-4-Methyloxazolidine-2,5-dione

Product 1

HCID 9855930(S)-3-benzoyl-4-methyl-2,5-oxazolidinedioneYield 74%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

4-Dimethylaminopyridine (61 mg, 0.5 mmol) and N-methylmorpholine (152 mg, 1.5 mmol) were dissolved in ethyl acetate (15 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 benzoyl chloride (281 mg, 2.0 mmol) in ethyl acetate (7 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 as white crystals (324 mg, 74%).

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-96b92b1de51b4a06a7c2e328ae01161c
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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