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

HRID 434125Notes

Reaction equation

HRID 434125 reaction equation
[CH3:1][C@H:2]1[C:6](=[O:7])[O:5][C:4](=[O:8])[NH:3]1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[C:9]([N:3]1[C@@H:2]([CH3:1])[C:6](=[O:7])[O:5][C:4]1=[O:8])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

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

Product 1

HCID 9855930(S)-3-benzoyl-4-methyl-2,5-oxazolidinedioneYield 80.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

(S)-4-Methyl-2,5-oxazolidinedione (L-alanine-NCA) (230 mg, 2.0 mmol) was dissolved in ethyl acetate (23 mL), followed by the addition of benzoyl chloride (365 mg, 2.6 mmol) under ice cooling. Further, a solution of 4-dimethylaminopyridine (318 mg, 2.6 mmol) in ethyl acetate (11 mL) was added dropwise under ice cooling over 20 minutes. After the resulting mixture was stirred as was at 0° C. for 3 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 (351 mg, 80%).

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-788eaa75492e4014936e4c4571c61bb0
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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