Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 66987908 | HCID 66987908 | — |
| Reactant | ethyl[2-(1H-imidazol-4-yl)ethyl]amine hydrochloride | HCID 178463864 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178463866 | HCID 178463866 | 105.4% |
Reaction Steps
0.14 g (0.38 mmol) of methyl(S)-3-(4-methoxyphenyl)-2-(4-nitrophenoxycarbonyl-amino)propionate is diluted in 2 mL of DMF. The solution is heated to 80° C. and 0.16 g (0.76 mmol) of ethyl[2-(1H-imidazol-4-yl)ethyl]amine hydrochloride and 0.13 mL (1.3 mmol) of diisopropylethylamine are then added. After 5 minutes, the reaction medium is cooled to room temperature and stirred for 15 minutes. Toluene is added and the solvents are evaporated off. The crude product obtained is chromatographed on silica gel (eluent: 8/2 dichloromethane/methanol). 0.15 g of methyl(S)-2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propionate in the form of a colourless oil is obtained in a yield of 100%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08877968B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-03d5dba057ec4eac8acbebaeced614f0 |
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| Source note | uspto-grants-2014_11 |
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