Ethanol → N6-Cyclopentyladenosine

HRID 1260156Notes

Reaction equation

HRID 1260156 reaction equation
Cl[C:2]1([NH2:20])[N:19]=[CH:18][N:17]=[C:16]2[C:3]1=[N:4][CH2:5][N:6]2[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[CH:21]1(N)[CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)C>CO>[CH:21]1([NH:20][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:16]=3[N:17]=[CH:18][N:19]=2)[C@@H:7]2[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 702EthanolHCID 2906CyclopentylamineHCID 666015536-Chloroadenosine

Product 1

HCID 657378N6-Cyclopentyladenosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-chloroadenosine (43 g) and cyclopentylamine (5 eq.) in ethanol (50 eq.) was heated at reflux for 3 hours then cooled to room temperature. The resultant reaction mixture was concentrated in vacuo and the resultant residue was diluted with water (400 ml) and ethyl acetate (400 ml). The organic layer was separated and the aqueous layer was extracted into ethyl acetate (2×400 ml). The combined organic layers were washed with water (2×200 ml), dried over sodium sulfate, concentrated in vacuo and dried under vacuum to provide a solid which was suspended in MeOH (400 mL), filtered and dried to provide N6-cyclopentyladenosine (43.8 g).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe resultant reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionthe resultant residue was diluted with water (400 ml) and ethyl acetate (400 ml)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted into ethyl acetate (2×400 ml)
  7. washThe combined organic layers were washed with water (2×200 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customdried under vacuum
  11. customto provide a solid which
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-784bf357a6c84acba5e64e6f2843422c
Source dataset
uspto-grants-2013_06
Patent number
US08470800B2

Reaction notes

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