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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 43575Generated: October 25, 2026

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

https://huagongshe.com/reaction/43575

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl N-(triethylammoniosulfonyl)carbamateHCID 2724994—
ReactantN-(4-Nitrobenzoyl)threonine methyl esterHCID 67548381—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 5-methyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylateHCID 67548873133.7%

Reaction Conditions

Temperature60 °C

Reaction Steps

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%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08536197B2
Source datasetuspto-grants-2013_09
ORD IDord-3aee7f1c53c04e828c91863938ab2990
Source noteuspto-grants-2013_09