HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methyl-4-nitrobenzoic acid → N-(3-Methyl-4-nitrobenzoyl)threonine methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methyl-4-nitrobenzoic acid | HCID 18370 | — |
| 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-Methyl-4-nitrobenzoyl)threonine methyl ester | HCID 67548938 | 900.1% |
Reaction Steps
The same operation as in Example (102a) was performed using threonine methyl ester hydrochloride (6.73 g, 39.6 mmol), 3-methyl-4-nitrobenzoic acid (7.18 g, 3.96 mmol), WSC hydrochloride (8.05 g, 42 mmol), DMAP (0.18 g, 1.5 mmol), N,N-diisopropylethylamine (5.42 g, 42 mmol) and dichloromethane (100 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/3, 2/3, 3/2, 3/1) to obtain 10.56 g of the title compound as a light yellow amorphous solid (90%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-5f81184728d14aea84083654c73cfc1b |
| Source note | uspto-grants-2013_09 |