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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 43625Generated: October 25, 2026

Methyl N-(triethylammoniosulfonyl)carbamate → Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate

https://huagongshe.com/reaction/43625

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl N-(triethylammoniosulfonyl)carbamateHCID 2724994—
ReactantN-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl esterHCID 68406078—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylateHCID 6754856286.3%

Reaction Steps

The same operation as in Example (97b) was performed using N-(4-{[(benzyloxy)carbonyl]amino}-3-methylbenzoyl)threonine methyl ester obtained in Example (108b) (5.37 g, 13.4 mmol), the Burgess reagent (4.0 g, 16.8 mmol) and THF (50 mL). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1) gave 4.42 g of the title compound as a colorless solid (86%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08536197B2
Source datasetuspto-grants-2013_09
ORD IDord-8931ace2eca04ecfb43d7be9d73e4202
Source noteuspto-grants-2013_09