1,2-Dichloroethane → N-(4-tert-Butyl-benzyl)-2-(3,4-diamino-phenyl)-propionamide

HRID 1626905Notes

Reaction equation

HRID 1626905 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:13])[C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[NH2:8].[C:14]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.O>[C:14]([C:18]1[CH:19]=[CH:20][C:21]([CH2:22][NH:23][C:10](=[O:12])[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([NH2:8])=[C:2]([NH2:1])[CH:3]=2)[CH3:13])=[CH:24][CH:25]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27356554-tert-ButylbenzylamineHCID 122268182-(3,4-Diaminophenyl)propanoic acid

Product 1

HCID 57742164N-(4-tert-Butyl-benzyl)-2-(3,4-diamino-phenyl)-propionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(3,4-Diaminophenyl)propanoic acid (436 mg, 2.42 mmol) in DMF (5 mL) was added 4-t-butylbenzylamine (399 mg, 2.44 mmol), EDC (702 mg, 3.66 mmol), HOBt (496 mg, 3.67 mmol), triethylamine (617 mg, 6.10 mmol) at 0 C. The reaction mixture was stirred for 16 hours at room temperature, and then the mixture was added water (50 mL) and extracted with methylene chloride. The organic layer was dried with MgSO4 and filtered. Methylene chloride was removed by evaporation. The residue was purified by column chromatography eluting with CH2Cl2/MeOH=20/1.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. customMethylene chloride was removed by evaporation
  5. customThe residue was purified by column chromatography
  6. washeluting with CH2Cl2/MeOH=20/1

Sources & evidence

ORD record
ord-1e6e17fba88f4577899d1c45e59b58f6
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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