Water → HCID 178460125, compound

HRID 660356Notes

Reaction equation

HRID 660356 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][NH:10][C:11](=[O:22])[CH:12]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH2:21])[CH:15]=2)[CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:25]([O-])=O.[Na+].O>C(O)(=O)C.CN(C=O)C>[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][NH:10][C:11](=[O:22])[CH:12]([C:14]2[CH:19]=[CH:18][C:17]3[NH:20][N:25]=[N:21][C:16]=3[CH:15]=2)[CH3:13])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 57742164N-(4-tert-Butyl-benzyl)-2-(3,4-diamino-phenyl)-propionamide

Product 1

HCID 178460125HCID 178460125, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

N-(4-tert-Butyl-benzyl)-2-(3,4-diamino-phenyl)-propionamide (110 mg, 0.338 mmol) in 5% aq. acetic acid (3 mL) and DMF (2.5 mL) was added sodium nitrite (30 mg, 0.435 mmol) at 0° C. The reaction mixture was stirred for 14 hours at room temperature. The mixture was added water (20 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=10/1.

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=10/1

Sources & evidence

ORD record
ord-c187e23bbd0042188546208e4ede26de
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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