4-Methylmorpholine → benzyl (4S)-4-ethyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate

HRID 1967285Notes

Reaction equation

HRID 1967285 reaction equation
[CH2:1]([C@H:3]1[C:7](=[O:8])[O:6][C:5](=[O:9])[NH:4]1)[CH3:2].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].CN1CCOCC1.C(OCC)(=O)C.Cl>O1CCCC1>[CH2:1]([C@H:3]1[C:7](=[O:8])[O:6][C:5](=[O:9])[N:4]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 10387Benzyl chloroformateHCID 21866389Hydrogen chloride-ethyl acetateHCID 54159673(s)-4-Ethyloxazolidine-2,5-dione

Product 1

HCID 59557010benzyl (4S)-4-ethyl-2,5-dioxo-1,3-oxazolidine-3-carboxylateYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (4S)-4-ethyl-1,3-oxazolidine-2,5-dione (69.57 g) and benzyl chloroformate (101.1 g) in tetrahydrofuran (800 mL) was cooled to 0° C., N-methylmorpholine (81.74 g) was added dropwise, and the mixture was stirred at 0° C. for 2 hr. A 4 mol/L hydrogen chloride-ethyl acetate solution (86.9 mL) was added dropwise at 0° C. to the reaction mixture, and the precipitated morpholine hydrochloride was filtered off with celite. The filtrate was concentrated under reduced pressure to give the title compound as a pale-yellow oil (yield: 91.58 g, 52%).

Workup

  1. filtrationthe precipitated morpholine hydrochloride was filtered off with celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b98d4e811744392b42c54446a6cdf64
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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