HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → Tert-butyl (trans-2-{4-[({3-[(phenylcarbonyl)amino]phenyl}carbonyl)amino]phenyl}-cyclopropyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 3-(benzoylamino)benzoic acid | HCID 256617 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate | HCID 86673140 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Tert-butyl (trans-2-{4-[({3-[(phenylcarbonyl)amino]phenyl}carbonyl)amino]phenyl}-cyclopropyl)carbamate | HCID 131734968 | 96.2% |
Reaction Steps
To a solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl]carbamate (124 mg) described in a document (J. Am. Chem. Soc., 2010, 132, 6827.) in acetonitrile (4 mL) were added 3-[(phenylcarbonyl)amino]benzoic acid (100 mg), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (95 mg), 1-hydroxybenzotriazole (67.2 mg) and triethylamine (69 μL). The mixture was stirred at room temperature overnight and water was added. Ethyl acetate was added to the mixture, and the resulting solid was collected by filtration to give the title compound (188 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278931B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-5c493d5eb41a48f49becf7576099a802 |
| Source note | uspto-grants-2016_03 |