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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 43633Generated: October 29, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-1,3-oxazole-4-carboxylate

https://huagongshe.com/reaction/43633

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantEthane, bromotrichloro-HCID 182782—
ReactantMethyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylateHCID 67548198—
SolventDichloromethaneHCID 6344—
ProductMethyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-1,3-oxazole-4-carboxylateHCID 6840585649.2%

Reaction Steps

The same operation as in Example (108d) was performed using methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate obtained in Example (109c) (1.43 g, 3.88 mmol), bromotrichloroethane (414 μL, 4.1 mmol), DBU (628 μL, 4.1 mmol) and dichloromethane (10 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1) to obtain 0.7 g of the title compound as a colorless solid (49%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08536197B2
Source datasetuspto-grants-2013_09
ORD IDord-78d9b82637da458285ee50f906232cb6
Source noteuspto-grants-2013_09