HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Salicylate → Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Salicylate | HCID 8365 | — |
| Reactant | 2-Dimethylaminopyridine | HCID 21885 | — |
| Reactant | 2-{[(Tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid | HCID 269698 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate | HCID 67173975 | 96.7% |
Reaction Steps
To a solution of ethyl 2-hydroxybenzoate (0.5 g, 3.0 mmol) in CH2Cl2 (8 mL) was added 2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (0.8 g, 3.0 mmol), EDCl (0.63 g, 3.3 mmol) and dimethylaminopyridine (0.037 g, 0.3 mmol). The reaction was stirred (RT, 3 h) and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2 and the combined organic extracts were dried over MgSO4. The crude material was purified by silica chromatography (0-10% MeOH/CH2Cl2) to afford 1.2 g of ethyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)benzoate. Mass calculated for C235H27NO6=413.46; found: [M+Na]+=437.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08173831B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-878aea62ae524171a43c4099461b0989 |
| Source note | uspto-grants-2012_05 |