Ethanol → Ccpa

HRID 1913857Notes

Reaction equation

HRID 1913857 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-4bfe4ffa490b4ff883963fa9a5aef81f
Source dataset
uspto-grants-2013_12
Patent number
US08609833B2

Reaction notes

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