Water → tert-Butyl {trans-2-[4-({[3-(trifluoromethyl)phenyl]carbonyl}amino)phenyl]cyclopropyl}-carbamate

HRID 922503Notes

Reaction equation

HRID 922503 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25].C(N(CC)CC)C.O>C(#N)C>[C:14]([O:13][C:12](=[O:18])[NH:11][C@@H:9]1[CH2:10][C@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:24]([C:23]2[CH:27]=[CH:28][CH:29]=[C:21]([C:20]([F:19])([F:30])[F:31])[CH:22]=2)=[O:25])=[CH:3][CH:4]=1)([CH3:15])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 86673140rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate

Product 1

HCID 86729841tert-Butyl {trans-2-[4-({[3-(trifluoromethyl)phenyl]carbonyl}amino)phenyl]cyclopropyl}-carbamateYield 95.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was crystallized (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b28a8bd3ae0c4ac7b79547b7016e2d52
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

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