HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → [4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 3-hydroxy-1,2,3-benzotriazin-4(3H)-one | HCID 73026 | — |
| Reactant | L-Methionine, methyl ester, hydrochloride | HCID 11435579 | — |
| Reactant | 2-(2-Methylphenyl)-4-nitrobenzoic acid | HCID 23436074 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [4-Nitro-2-(2-methylphenyl)benzoyl]methionine methyl ester | HCID 53719134 | 99.4% |
Reaction Steps
The product of Example 308A (604 mg, 2.35 mmol) and HOOBT (574 mg, 3.52 mmol) were dissolved in DMF (10 mL) and methionine methyl ester HCl (679 mg, 3.52 mmol) and EDCI (676 mg, 3.52 mmol) were added followed by Et3N (476 mg, 0.65 mL, 4.7 mmol). The reaction was stirred for 12 hours and then was taken up in ethyl acetate and washed successively with brine (3×) and water (3×). The ethyl acetate layer was dried over Na2SO4, filtered and evaporated. Purification by chromatography on silica gel (5% methanol-ethyl acetate) gave the desired compound (940 mg, 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06693123B2 |
| Source dataset | uspto-grants-2004_02 |
| ORD ID | ord-0aa2890e021e459dbc184aa991d60333 |
| Source note | uspto-grants-2004_02 |