4-Methylmorpholine → (S)-3-(3-phenylpropanoyl)-4-methyl-2,5-oxazolidinedione

HRID 434132Notes

Reaction equation

HRID 434132 reaction equation
[CH3:1][C@H:2]1[C:6](=[O:7])[O:5][C:4](=[O:8])[NH:3]1.[C:9]1([CH2:15][CH2:16][C:17](Cl)=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN1CCOCC1>C(OCC)(=O)C>[C:9]1([CH2:15][CH2:16][C:17]([N:3]2[C@@H:2]([CH3:1])[C:6](=[O:7])[O:5][C:4]2=[O:8])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 64801Benzenepropanoyl chlorideHCID 10996998(S)-4-Methyloxazolidine-2,5-dione

Product 1

HCID 59119731(S)-3-(3-phenylpropanoyl)-4-methyl-2,5-oxazolidinedioneYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(S)-4-methyl-2,5-oxazolidinedione (L-alanine-NCA) (345 mg, 3 mmol) was dissolved in ethyl acetate (20 mL), followed by the addition of 3-phenylpropanoyl chloride (658 mg, 3.9 mmol) under ice cooling. Further, a solution of N-methyl-morpholine (394 mg, 3.9 mmol) in ethyl acetate (10 mL) was added dropwise under ice cooling over 20 minutes, and the resulting mixture was then stirred at the same temperature for 2 hours. The reaction mixture was treated in a similar manner as in Synthesis Process 5 of Example 8 to afford the title compound (408 mg, 55%) as a colorless clear syrup.

Workup

  1. additionThe reaction mixture was treated in a similar manner as in Synthesis Process 5 of Example 8

Sources & evidence

ORD record
ord-e4d415af27a24464a60ad98809652090
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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