Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 2-Dimethylaminopyridine | HCID 21885 | — |
| Reactant | 4-Bromomethyl-3-nitrobenzoic acid | HCID 132386 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Glycine ethyl ester, hydrochloride | HCID 2723640 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22632621 | HCID 22632621 | — |
Reaction Steps
2.5 g (9.6 mmol) of 3-nitro-4-bromomethylbenzoic acid was dissolved in 100 ml of dichloromethane. 0.78 ml (19.2 mmol) of methanol, 2.2 g (11.5 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-3-carbodiimide hydrochloride and 30 mg of dimethylaminopyridine were added to the obtained solution, and they were stirred at room temperature for 3 hours. The reaction mixture was treated with dichloromethane as the extracting solvent by an ordinary method to obtain the crude product. The crude product was dissolved in 50 ml of THF. 2.0 g (14.6 mmol) of glycine ethyl ester hydrochloride and 1.8 g (21.9 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 80° C. for 4 hours. The insoluble matter was removed by the filtration, and the solvent was evaporated. After the extraction with ethyl acetate followed by the treatment by an ordinary method, the crude title compound was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06825191B2 |
|---|
| Source dataset | uspto-grants-2004_11 |
|---|
| ORD ID | ord-4d65a7bf1b094ce7a67e50fdb4a8dcaf |
|---|
| Source note | uspto-grants-2004_11 |
|---|