Hydrochloric Acid → Deoxyadenosine

HRID 1679035Notes

Reaction equation

HRID 1679035 reaction equation
C([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[CH2:8][C@@H:7]1[OH:21])(=O)C.Cl.[OH-].[Na+]>CO>[C@@H:9]1([N:11]2[C:20]3[N:19]=[CH:18][N:17]=[C:15]([NH2:16])[C:14]=3[N:13]=[CH:12]2)[O:10][C@H:6]([CH2:5][OH:4])[C@@H:7]([OH:21])[CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14506332HCID 14506332, compound

Product 1

HCID 13730Deoxyadenosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 5'-O-acetyl-2'-deoxyadenosine (0.200 gms.) in methanol (15 ml.), add dilute hydrochloric acid (10 ml., 1 N) and allow the reaction mixture to stand at room temperature for 24 hours. Bring the solution to a neutral pH by the careful addition of dilute sodium hydroxide (2%). Filter any precipitated salts and wash the filtrate with pyridine. Concentrate the combined filtrate and pyridine washings in vacuo and recrystallize the resultant residue from methanol:water to give 2'-deoxyadenosine; m.p. 183°-188° C; [α]D22 -25° (water, c=0.4).

Workup

  1. filtrationFilter any precipitated salts
  2. washwash the filtrate with pyridine
  3. concentrationConcentrate the combined filtrate and pyridine washings in vacuo
  4. customrecrystallize the resultant residue from methanol

Sources & evidence

ORD record
ord-2e925a88d7af47fa8be62ab93692aacc
Source dataset
uspto-grants-1978_03
Patent number
US04078139

Reaction notes

Loading…