HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → tert-Butyl {trans-2-[4-({[3-(trifluoromethyl)phenyl]carbonyl}amino)phenyl]cyclopropyl}-carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Trifluoromethyl)benzoyl chloride | HCID 75257 | — |
| Reactant | rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate | HCID 86673140 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | tert-Butyl {trans-2-[4-({[3-(trifluoromethyl)phenyl]carbonyl}amino)phenyl]cyclopropyl}-carbamate | HCID 86729841 | 95.1% |
Reaction Steps
To a solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl]carbamate (100 mg) described in a document (J. Am. Chem. Soc., 2010, 132, 6827.) in acetonitrile (4 mL) were added 3-(trifluoromethyl)benzoyl chloride (126 mg) and triethylamine (84 μL). The mixture was stirred at room temperature for 30 min and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was crystallized (hexane/ethyl acetate) to give the title compound (161 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278931B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-b28a8bd3ae0c4ac7b79547b7016e2d52 |
| Source note | uspto-grants-2016_03 |