Diethyl Ether → HCID 86588795, compound

HRID 1796127Notes

Reaction equation

HRID 1796127 reaction equation
[N:1]1([CH2:10][C:11]2[N:15]([CH2:16][CH2:17][C:18]([NH:20]O)=[NH:19])[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[C:26]([O:29]C(=O)C)(=[O:28])[CH3:27].C(OCC)C>C(O)(=O)C.[Pd]>[C:26]([OH:29])(=[O:28])[CH3:27].[C:26]([OH:29])(=[O:28])[CH3:27].[N:1]1([CH2:10][C:11]2[N:15]([CH2:16][CH2:17][C:18]([NH2:20])=[NH:19])[C:14]3[CH:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 178511104HCID 178511104, compound

Product 1

HCID 86588795HCID 86588795, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-[3-(2-Benzotriazol-1-ylmethyl-benzimidazol-1-yl)-1-imino-propyl)-hydroxyamine (57 mg, 0.17 mmol) was dissolved in acetic acid (1 mL). Acetic anhydride was added and the solution was stirred at room temperature for 5–10 minutes. The solution was then added to 10% Pd/C (15 mg) in a Parr reaction vessel. The mixture was agitated under H2 (at 55 psi) for 4 hours. The catalyst was removed by filtration. Evaporation of the filtrate gave a yellow gum which was azeotroped with hexane several times. Trituration with diethyl ether gave 64 mg (64% yield) of the title compound as a tan solid.

Workup

  1. stirringThe mixture was agitated under H2 (at 55 psi) for 4 hours
  2. customThe catalyst was removed by filtration
  3. customEvaporation of the filtrate
  4. customgave a yellow gum which
  5. customwas azeotroped with hexane several times

Sources & evidence

ORD record
ord-fe7d5b9629d64e77a9d61827912edd66
Source dataset
uspto-grants-2006_04
Patent number
US07030140B2

Reaction notes

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