Water → HCID 178460125, compound

HRID 1626906Notes

Reaction equation

HRID 1626906 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-b0136163b70448da910708aadfb8b703
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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