Ethanol → N6-Cyclopentyladenosine

HRID 30501Notes

Reaction equation

HRID 30501 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 eoganic 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 eoganic 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-76e3fc0a7431444e9249f4953bb3d5a8
Source dataset
uspto-grants-2008_09
Patent number
US07423144B2

Reaction notes

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