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

HRID 922524Notes

Reaction equation

HRID 922524 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[C:19]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][CH:22]=[C:21]([C:25](Cl)=[O:26])[CH:20]=1.C(N(CC)CC)C.O>C(#N)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:25]([C:21]2[CH:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[O:26])=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2756666Biphenyl-3-carbonyl chlorideHCID 86673140rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate

Product 1

HCID 131734971tert-Butyl(trans-2-{4-[(biphenyl-3-ylcarbonyl)amino]phenyl}cyclopropyl)carbamateYield 89.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

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 biphenyl-3-carbonyl chloride (131 mg) and triethylamine (61.1 mg). The mixture was stirred at room temperature overnight and water was added. To the reaction mixture was added ethyl acetate, and the resulting solid was collected by filtration to give the title compound (154 mg).

Workup

  1. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-f598a6fcc119470ba1ba8f802e968ead
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

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