M-Phenylenediamine → HCID 90052375, compound

HRID 2284644Notes

Reaction equation

HRID 2284644 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:26]1([NH2:33])[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[CH:27]=1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C.C(OCC)(=O)C>[NH2:32][C:28]1[CH:27]=[C:26]([NH:33][C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 7935M-PhenylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 516892Sodium Bicarbonate

Product 1

HCID 90052375HCID 90052375, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Procedure

To a solution of N-Boc-β-alanine (1.00 g) in N,N-dimethylactamide (5 mL), carbonyldiimidazole (888 mg) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour and 20 minutes. To the reaction mixture, a solution of 1,3-phenylenediamine (1.15 g) in N,N-dimethylactamide (5 mL) was added at room temperature, and the mixture was stirred at the same temperature for 18 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain tert-butyl (3-((3-aminophenyl)amino)-3-oxopropyl)carbamate (B6, 978 mg).

Workup

  1. stirringthe mixture was stirred at the same temperature for 18 hours
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-61a7e208ba59411d8b6b46ef8b8b1523
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…