Acetic Acid → Peldesine

HRID 496831Notes

Reaction equation

HRID 496831 reaction equation
C([N:5]([C:13]1[C:17]([CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][NH:15][C:14]=1[C:25]([O:27]C)=O)[C:6]([NH:8]C(OC)=O)=[NH:7])(OC)=O.[OH-].[Na+].C(O)(=O)C>CO>[NH2:7][C:6]1[NH:8][C:25](=[O:27])[C:14]2[NH:15][CH:16]=[C:17]([CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[C:13]=2[N:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 140382078HCID 140382078, compound

Product 1

HCID 135413525PeldesineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(N,N′-bis-carbomethoxyguanidinyl)-4-(3-pyridylmethyl)-1H-pyrrole-2-carboxylate, obtained from Example 26 (15.0 g, 0.04 mol), methanol (100 mL) and sodium hydroxide pellets (3.7 g, 0.9 mol) were stirred together and boiled under reflux for 18 hours. The mixture was cooled, neutralized with acetic acid (5.4 g. 0.09 mol) and the solid collected by filtration. The product was washed in turn with methanol (20 mL), water (200 mL) and methanol (30 mL) and dried at 110° C. overnight to give 8.2 g (88%) of an off-white powder, mp>300° C.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe solid collected by filtration
  4. washThe product was washed in turn with methanol (20 mL), water (200 mL) and methanol (30 mL)
  5. customdried at 110° C. overnight

Sources & evidence

ORD record
ord-2cf8bf3d251c4e7da8d7ba2d52b94d35
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

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