HCID 86729715, compound → HCID 86729714, compound

HRID 875368Notes

Reaction equation

HRID 875368 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:6]([NH:8][CH:9]=[N:10][C:11](=[O:28])[O:12][N:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([N+:21]([O-])=O)[CH:15]=1)=[O:7]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[C:6]([NH:8][CH:9]=[N:10][C:11](=[O:28])[O:12][N:13]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([NH2:21])[CH:15]=1)=[O:7]

Participants

4

Reactant 1

HCID 86729715HCID 86729715, compound

Product 1

HCID 86729714HCID 86729714, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a bottle, a mixture of Boc nitro-guanidine (4) (1.22 g, 2.5 mmol) in MeOH (80 mL) and Pd/C 10% (100 mg) is stirred under H2 at 50 psi for 10 hours. The starting substrate has disappeared; the catalyst is filtered and the solvent is evacuated under vacuum. The residue is purified by column chromatography, eluting with Hept/EtOAc mixture: 7/3, obtaining the title compound as yellow oil (5) (840 mg, 73%).

Workup

  1. filtrationthe catalyst is filtered
  2. customthe solvent is evacuated under vacuum
  3. customThe residue is purified by column chromatography
  4. washeluting with Hept/EtOAc mixture

Sources & evidence

ORD record
ord-08b80d31e9bc4f2e9e7adba8850d59a5
Source dataset
uspto-grants-2015_03
Patent number
US08981149B2

Reaction notes

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