1-Propanol → HCID 14842842, compound

HRID 2255896Notes

Reaction equation

HRID 2255896 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[OH-].[Na+].[CH2:23]([OH:26])[CH2:24][CH3:25]>>[CH2:23]([O:26][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])[CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 89742-ChloroadenosineHCID 14798Sodium Hydroxide

Product 1

HCID 14842842HCID 14842842, compound

Procedure

2-Chloro-adenosine (3.5 g) was added to a hot solution of NaOH (3.2 g) in n-propanol (80 ml), the mixture was heated under reflux for 3 hours. The volatiles were removed in vacuo, the residue taken into water (40 ml), cooled and acidified with 1M hydrochloric acid to pH 7. After 15 min the suspension was filtered and the filtrate evaporated. The residue was taken up in ethanol, and adsorbed onto silica which was placed on a chromatography column. Elution with 9:1, and then 4:1 CHCl3 afforded the sub-title compound (0.65 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customThe volatiles were removed in vacuo
  4. temperaturecooled
  5. filtrationAfter 15 min the suspension was filtered
  6. customthe filtrate evaporated
  7. washElution with 9:1

Sources & evidence

ORD record
ord-e8acac7835bd4a15971b25f682a32f8d
Source dataset
uspto-grants-1997_08
Patent number
US05654285

Reaction notes

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