Hydrochloric Acid → HCID 135524536, compound

HRID 1459172Notes

Reaction equation

HRID 1459172 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2)([O:6]CC)=[O:5])[CH3:2].Cl>[OH-].[Na+]>[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:18](=[O:22])[NH:17][C:16]([NH2:23])=[N:15][C:14]1=2)([OH:6])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135404759HCID 135404759, compound

Product 1

HCID 135524536HCID 135524536, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

9-(2-(diethylphosphonomethoxy)ethyl)guanine (0.198 g, 0.57 mmol) was dissolved in 15 mL of 1N sodium hydroxide solution and the mixture was stirred at room temperature for 1 hour. The solution was then acidified with 10% aqueous hydrochloric acid to pH 1 and concentrated in vacuo. Residual salts were removed by reverse phase column chromatography (C18 adsorbent, elution with water) to provide 0.150 g of 9-(2-(ethylphosphonomethoxy)ethyl)-guanine as a white crystalline solid, mp=192.5°-193.5° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customResidual salts were removed by reverse phase column chromatography (C18 adsorbent, elution with water)

Sources & evidence

ORD record
ord-de1d2252751e48849871aea56b7e9c1b
Source dataset
uspto-grants-1998_12
Patent number
US05854228

Reaction notes

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