HCID 178479430, compound → HCID 178479434, compound

HRID 981331Notes

Reaction equation

HRID 981331 reaction equation
[ClH:1].C([O:9][CH:10]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28]([NH2:30])=[NH:29])[C:11](=[O:18])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[ClH:1].[NH:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20](=[O:31])[NH:19][CH:10]([OH:9])[C:11](=[O:18])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[C:28]([NH2:30])=[NH:29]

Participants

4

Reactant 1

HCID 178479430HCID 178479430, compound

Product 1

HCID 178479434HCID 178479434, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

0.65 g (1.42 mmol) of 7-benzyloxy-15-guanidino-1-hydroxy-5,8-diazapentadecane-6,9-dione hydrochloride was dissolved in 20 ml of 1N acetic acid and catalytically reduced in the presence of 0.2 g of palladium black under a hydrogen pressure of 10 kg/cm2 at room temperature for 36 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 product were combined and concentrated to dryness under reduced pressure. 90% ethanol was added to the residue and the insoluble sodium chloride was filtered off. The filtrate was then passed through a column packed with 100 ml of Sephadex® LH-20 and eluted with 90% ethanol. Fractions containing the aimed compound were combined and concentrated to dryness under reduced pressure. The residue was dissolved in a small amount of distilled water and the insoluble matters were filtered off. The obtained aqueous solution was lyophilized to thereby give 0.497 g of the aimed compound (yield: 95.1%).

Workup

  1. customat room temperature
  2. customfor 36 hours
  3. filtrationAfter filtering off the catalyst
  4. wash(Na) and subjected to gradient elution between 500 ml of distilled water and 500 ml of 0.3M sodium chloride
  5. additionFractions containing the aimed product
  6. concentrationconcentrated to dryness under reduced pressure
  7. addition90% ethanol was added to the residue
  8. filtrationthe insoluble sodium chloride was filtered off
  9. washeluted with 90% ethanol
  10. additionFractions containing the aimed compound
  11. concentrationconcentrated to dryness under reduced pressure
  12. dissolutionThe residue was dissolved in a small amount of distilled water
  13. filtrationthe insoluble matters were filtered off

Sources & evidence

ORD record
ord-046608d2c48e462c9f3dd171c3c492d2
Source dataset
uspto-grants-1991_02
Patent number
US04990536

Reaction notes

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