Dimethylformamide → HCID 178512810, compound

HRID 981332Notes

Reaction equation

HRID 981332 reaction equation
Cl.C([O:9][CH:10]([NH:27][C:28](=[O:39])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([NH2:38])=[NH:37])[C:11](=[O:26])[NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC1C=CC=CC=1)=[O:17])C1C=CC=CC=1.CN(C)C=O>C(O)(=O)C.[Pd]>[NH:35]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][C:28](=[O:39])[NH:27][CH:10]([OH:9])[C:11](=[O:26])[NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:36]([NH2:38])=[NH:37]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 178479431HCID 178479431, compound

Product 1

HCID 178512810HCID 178512810, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

0.79 g (1.41 mmol) of benzyl 7-benzyloxy-15-guanidino-6,9-dioxo-5,8-diazapentadecanoate hydrochloride was dissolved in 10 ml of 1N acetic acid and 10 ml of dimethylformamide and catalytically reduced in the presence of palladium black at room temperature under a hydrogen pressure of 10 kg/cm2 for 34 hours. After filtering off the catalyst, the filtrate was adsorbed on 100 ml of CM-Sephadex® C-25 (Na) and subjected to gradient elution between 500 ml of distilled water and 500 ml of 0.3M sodium chloride. Fractions containing the aimed compound were combined and concentrated to dryness under reduced pressure. 90% ethanol was added to the residue and the insoluble sodium chloride was filtered off. Next, the filtrate was subjected to gradient elution between 500 ml of distilled water and 500 ml of a 30% aqueous solution of acetone by using a column packed with 100 ml of Diaion® HP-20. Fractions containing the aimed compound were combined and concentrated under reduced pressure. The residue was dissolved in a small amount of distilled water and the insoluble matters were filtered off. By lyophilizing the product, 0.280 g of the aimed compound was obtained (yield: 57.8%).

Workup

  1. customfor 34 hours
  2. filtrationAfter filtering off the catalyst
  3. wash(Na) and subjected to gradient elution between 500 ml of distilled water and 500 ml of 0.3M sodium chloride
  4. additionFractions containing the aimed compound
  5. concentrationconcentrated to dryness under reduced pressure
  6. addition90% ethanol was added to the residue
  7. filtrationthe insoluble sodium chloride was filtered off
  8. washNext, the filtrate was subjected to gradient elution between 500 ml of distilled water and 500 ml of a 30% aqueous solution of acetone
  9. additionFractions containing the aimed compound
  10. concentrationconcentrated under reduced pressure
  11. dissolutionThe residue was dissolved in a small amount of distilled water
  12. filtrationthe insoluble matters were filtered off

Sources & evidence

ORD record
ord-46ad4422f9db4052b714c5af7b4e9916
Source dataset
uspto-grants-1991_02
Patent number
US04990536

Reaction notes

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