HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylamine → tert-Butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 2-(4-Chlorophenyl)ethylamine | HCID 67430 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 4-(4-(2-Tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid | HCID 68468397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl 2-(4-(4-(4-chlorophenethylcarbamoyl)phenoxy)-3-cyanophenyl)acetate | HCID 68467179 | 85% |
Reaction Steps
To 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoic acid (0.34 g, 0.962 mmol), 2-(4-chlorophenyl)ethanamine (0.165 g, 1.06 mmol) in DMF (5 ml) was added diisopropylamine (0.200 ml, 1.15 mmol) and HBTU (0.149 g, 1.15 mmol). The reaction was stirred at ambient temperature for 90 minutes. The reaction was diluted with water and the product extracted into ethyl acetate. The combined organic layers were dried (MgSO4), filtered and concentrated to give tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)acetate (0.40 g, 85%) as a white solid after column chromatography.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08183289B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-60301368e7194c0180672f9eabb897f8 |
| Source note | uspto-grants-2012_05 |