Methyl N-(triethylammoniosulfonyl)carbamate → Methyl 5-methyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate

HRID 43575Notes

Reaction equation

CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[CH3:16][O:17][C:18](=[O:35])[C@H:19]([C@@H:32]([CH3:34])[OH:33])[NH:20][C:21](=O)[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1>C1COCC1>[CH3:34][CH:32]1[O:33][C:21]([C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[N:20][CH:19]1[C:18]([O:17][CH3:16])=[O:35]

Participants

Conditions

Temperature: 60 °C

Procedure

The Burgess reagent (0.60 g, 2.5 mmol) was added to a solution of N-(4-nitrobenzoyl)threonine methyl ester obtained in Example (97a) (0.57 g, 3 mmol) in THF (20 mL), and the mixture was stirred at 60° C. for two hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 1/2) to obtain 1.06 g of the title compound as a colorless solid (100%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 1/2)

Sources & evidence

ORD record: ord-3aee7f1c53c04e828c91863938ab2990
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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