HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Methyl-4-nitrobenzoic acid → N-(3-Methyl-4-nitrobenzoyl)serine methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Methyl-4-nitrobenzoic acid | HCID 18370 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | L-Serine, methyl ester, hydrochloride (1:1) | HCID 2723730 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-(3-Methyl-4-nitrobenzoyl)serine methyl ester | HCID 67549024 | 88% |
Reaction Steps
The same operation as in Example (102a) was performed using serine methyl ester hydrochloride (5.24 g, 33.7 mmol), 3-methyl-4-nitrobenzoic acid (6.1 g, 33.7 mmol), WSC hydrochloride (6.71 g, 35 mmol), DMAP (0.18 g, 1.5 mmol), N,N-diisopropylethylamine (4.52 g, 35 mmol) and dichloromethane (100 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 1/0) to obtain 8.35 g of the title compound as a light yellow solid (88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-2faf7fa1bb3c4780a2f7cac8f2e75aea |
| Source note | uspto-grants-2013_09 |