Ethanol → Ccpa

HRID 30500Notes

Reaction equation

HRID 30500 reaction equation
C(O[C@@:5]1([OH:33])[C@:9](OC(=O)C)([OH:10])[C@@H:8]([CH:15](OC(=O)C)[OH:16])[O:7][C@H:6]1[N:21]1[C:30]2[C:24]([C:25](Cl)([N:27]=[C:28]([Cl:31])[N:29]=2)[NH2:26])=[N:23][CH2:22]1)(=O)C.[CH:34]1(N)[CH2:38][CH2:37][CH2:36][CH2:35]1.C(O)C>C(OCC)(=O)C.O>[Cl:31][C:28]1[N:27]=[C:25]([NH:26][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:24]2[N:23]=[CH:22][N:21]([C:30]=2[N:29]=1)[C@@H:6]1[O:7][C@H:8]([CH2:15][OH:16])[C@@H:9]([OH:10])[C@H:5]1[OH:33]

Participants

6

Reactant 3

HCID 702EthanolHCID 2906CyclopentylamineHCID 68406760HCID 68406760, compound

Product 1

HCID 123807Ccpa

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2′,3′,5′-triacetoxy-2,6-dichloroadenosine (1.5 g) and cyclopentylamine (8 eq.) were diluted with ethanol (50 eq.) and the resulting solution was heated at reflux for about 15 hours, then cooled to room temperature and concentrated in vacuo to provide a crude residue which was diluted with a mixture of ethyl acetate and water and transferred to a separatory funnel. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to provide a crude residue which was purified using flash column chromatography on silica gel (8% MeOH-dichloromethane as eluent) to provide 2-chloro-N6-cyclopentyladenosine (0.948 g). MS m/z 370.32 [M+H]+.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for about 15 hours
  3. concentrationconcentrated in vacuo
  4. customto provide a crude residue which
  5. customtransferred to a separatory funnel
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto provide a crude residue which
  10. customwas purified

Sources & evidence

ORD record
ord-e91e73d6a5614a31a21e68c1b13e74d7
Source dataset
uspto-grants-2008_09
Patent number
US07423144B2

Reaction notes

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