HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methoxy-4-nitrobenzoic acid → N-(3-Methoxy-4-nitrobenzoyl)threonine methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methoxy-4-nitrobenzoic acid | HCID 78764 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | Methyl L-threoninate hydrochloride | HCID 2734893 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(3-Methoxy-4-nitrobenzoyl)threonine methyl ester | HCID 67549208 | 95% |
Reaction Steps
The same operation as in Example (102a) was performed using threonine methyl ester hydrochloride (2.88 g, 17 mmol), 3-methoxy-4-nitrobenzoic acid (3 g, 15.2 mmol), WSC hydrochloride (3.83 g, 20 mmol), DMAP (0.18 g, 1.5 mmol), N,N-diisopropylethylamine (2.58 g, 20 mmol) and dichloromethane (40 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 2/1, 1/0) to obtain 4.49 g of the title compound as a light yellow amorphous solid (95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-e340d1576ca54290a3f1d7e443e7d790 |
| Source note | uspto-grants-2013_09 |