1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Oxanosine

HRID 5146Notes

Reaction equation

HRID 5146 reaction equation
Cl.CN(C)CCC[N:7]=[C:8]=[N:9]CC.NC(N[C:17]1[N:18]([C@@H:25]2[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]2[OH:27])[CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=1)=O>O.CO>[CH:17]1[N:18]([C@@H:25]2[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]2[OH:27])[C:19]2[N:7]=[C:8]([NH2:9])[O:24][C:22](=[O:23])[C:20]=2[N:21]=1

Participants

5

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131718114[(amino)carbonyl]amino-1-(beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 477547Oxanosine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg, 0.41 mmol) was added to a solution of 5-[[(amino)carbonyl]amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid (19 mg, 0.063 mmol) in water (2 mL) and CH3OH (5 mL) and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of excess 60% aqueous acetic acid. After 30 minutes, the mixture was diluted with water, concentrated to remove CH3OH and lyophilized. The resulting powder (100 mg) was chromatographed on reverse phase silica gel [10 g, flash, stepwise gradient elution: water (200 mL), 10% CH3OH in water (v/v, 100 mL), 20% CH3OH in water (v/v, 100 mL), 10-mL fractions]. Fractions containing the product were combined, concentrated under reduced pressure and lyophilized to give oxanosine: 16 mg (89%).

Workup

  1. customThe reaction was quenched by addition of excess 60% aqueous acetic acid
  2. waitAfter 30 minutes
  3. additionthe mixture was diluted with water
  4. concentrationconcentrated
  5. customto remove CH3OH
  6. customThe resulting powder (100 mg) was chromatographed on reverse phase silica gel [
  7. wash10 g, flash, stepwise gradient elution
  8. additionFractions containing the product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b09968f7a78948329b0580e276d90a67
Source dataset
uspto-grants-1993_09
Patent number
US05243042

Reaction notes

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