Triethylamine → Tert-butyl(cyclopropylmethyl)(trans-2-{4-[(4-methylbenzoyl)amino]phenyl}cyclopropyl)carbamate

HRID 922534Notes

Reaction equation

HRID 922534 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[N:11]([CH2:19][CH:20]2[CH2:22][CH2:21]2)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30]1([CH3:39])[CH:35]=[CH:34][C:33]([C:36](Cl)=[O:37])=[CH:32][CH:31]=1.[Cl-].[NH4+]>C1COCC1>[C:14]([O:13][C:12](=[O:18])[N:11]([CH2:19][CH:20]1[CH2:22][CH2:21]1)[C@@H:9]1[CH2:10][C@H:8]1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:36](=[O:37])[C:33]2[CH:34]=[CH:35][C:30]([CH3:39])=[CH:31][CH:32]=2)=[CH:3][CH:4]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 25517Ammonium ChlorideHCID 86729891Tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate

Product 1

HCID 86729894Tert-butyl(cyclopropylmethyl)(trans-2-{4-[(4-methylbenzoyl)amino]phenyl}cyclopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (75.0 mg) and triethylamine (41.5 μL) in THF (1.24 mL) was added 4-toluoyl chloride (39.4 μL). The mixture was stirred at room temperature overnight, and poured into saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (104.3 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8b528311936a4626a863f846138eb8f1
Source dataset
uspto-grants-2016_03
Patent number
US09278931B2

Reaction notes

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