HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-1,3-oxazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Ethane, bromotrichloro- | HCID 182782 | — |
| Reactant | Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate | HCID 67548198 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-1,3-oxazole-4-carboxylate | HCID 68405856 | 49.2% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-78d9b82637da458285ee50f906232cb6 |
| Source note | uspto-grants-2013_09 |