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

HRID 922494Notes

Reaction equation

HRID 922494 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.[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].C(N(CC)CC)C.O>C(#N)C>[Br:19][C:20]1[CH:21]=[C:22]([C:23]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[CH2:10][C@H:9]3[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:4][CH:3]=2)=[O:24])[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-HCID 86673140rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate

Product 1

HCID 86729828Tert-butyl [trans-2-(4-{[(3-bromophenyl)carbonyl]amino}phenyl)cyclopropyl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

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 purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5a63a772ccbf4e7b841e503919db5ca3
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

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