HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Tert-butyl [trans-2-(4-{[(3-bromophenyl)carbonyl]amino}phenyl)cyclopropyl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzoyl chloride, 3-bromo- | HCID 74377 | — |
| 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-bromophenyl)carbonyl]amino}phenyl)cyclopropyl]carbamate | HCID 86729828 | — |
Reaction Steps
To a solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl]carbamate (300 mg) described in a document (J. Am. Chem. Soc., 2010, 132, 6827.) in acetonitrile (12 mL) were added 3-bromobenzoyl chloride (191 μL) and triethylamine (202 μL). The mixture was stirred at room temperature overnight 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 purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (407 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278931B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-5a63a772ccbf4e7b841e503919db5ca3 |
| Source note | uspto-grants-2016_03 |