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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 922494Generated: October 30, 2026

Water → Tert-butyl [trans-2-(4-{[(3-bromophenyl)carbonyl]amino}phenyl)cyclopropyl]carbamate

https://huagongshe.com/reaction/922494

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTriethylamineHCID 8471—
ReactantBenzoyl chloride, 3-bromo-HCID 74377—
Reactantrac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamateHCID 86673140—
SolventAcetonitrileHCID 6342—
ProductTert-butyl [trans-2-(4-{[(3-bromophenyl)carbonyl]amino}phenyl)cyclopropyl]carbamateHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278931B2
Source datasetuspto-grants-2016_03
ORD IDord-5a63a772ccbf4e7b841e503919db5ca3
Source noteuspto-grants-2016_03