HCID 69592311, compound → HCID 69592294, compound

HRID 325030Notes

Reaction equation

HRID 325030 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=[CH:15][CH:16]=2)=[C:4]([CH:20]=[N:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:3]=1>CCO.[Pd]>[NH2:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][C:4]=2[CH:20]=[N:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:12]=1

Participants

4

Reactant 1

HCID 69592311HCID 69592311, compound

Product 1

HCID 69592294HCID 69592294, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-[2-(4-amino{t-butoxycarbonylimino}methylphenyl)-ethoxy]nitrobenzene (1.47 g; 3.81 mmol; from step (iii) above) and Pd (0.236 g; 5% on charcoal) in EtOH (75 mL) was stirred under H2(g) (1 atm.) for 25 minutes. After filtration through Celite the solvent was evaporated. The residue was purified by preparative HPLC (60% CH3CN/aq:0.1M NH4OAc) to afford the sub-title compound. Yield: 1.02 g (75%).

Workup

  1. filtrationAfter filtration through Celite the solvent
  2. customwas evaporated
  3. customThe residue was purified by preparative HPLC (60% CH3CN/aq:0.1M NH4OAc)

Sources & evidence

ORD record
ord-f3efa4e37f874cebb02fd3f8e54d0e7d
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

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