Acetyl chloride → HCID 45086078, compound

HRID 434129Notes

Reaction equation

HRID 434129 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:11])[CH3:10].CN1CCOCC1>C(OCC)(=O)C>[C:9]([N:3]1[C@@H:2]([CH3:1])[C:6](=[O:7])[O:5][C:4]1=[O:8])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 10996998(S)-4-Methyloxazolidine-2,5-dione

Product 1

HCID 45086078HCID 45086078, compoundYield 74.3%

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 acetyl chloride (306 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. 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 chloroform (5 mL), and insoluble matter was filtered off. The filtrate was concentrated under reduced pressure to afford the title compound (350 mg, 74%) 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 chloroform (5 mL)
  4. filtrationinsoluble matter was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f065dd6c2b214e478a2bad341c7c4695
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

Loading…