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

HRID 1626864
Notes
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Reaction equation

HRID 1626864 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-ca90899431d94a6e844499897156b422
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785474B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes