HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl N-(triethylammoniosulfonyl)carbamate → Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl N-(triethylammoniosulfonyl)carbamate | HCID 2724994 | — |
| Reactant | N-(4-{[(Benzyloxy)carbonyl]amino}-3-methylbenzoyl)serine methyl ester | HCID 67548569 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 2-(4-{[(benzyloxy)carbonyl]amino}-3-methylphenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate | HCID 67548198 | 83.3% |
Reaction Steps
The same operation as in Example (97b) was performed using N-(4-{[(benzyloxy)carbonyl]amino}-3-methylbenzoyl)serine methyl ester obtained in Example (109b) (1.8 g, 4.66 mmol), the Burgess reagent (1.44 g, 6.06 mmol) and THF (15 mL). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1) gave 1.43 g of the title compound as a colorless solid (83%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-ca215d57cb904325812389538b996b1f |
| Source note | uspto-grants-2013_09 |