Adenosine → HCID 135450943, compound

HRID 974772Notes

Reaction equation

HRID 974772 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:16][C@H:15]([OH:17])[C@@H:14]([CH2:18][OH:19])[O:13][CH2:12]2)=[C:4](Cl)[N:3]=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:23]>P([O-])([O-])([O-])=O>[NH:3]1[C:4](=[O:23])[C:5]2[N:6]=[CH:7][N:8]([C@H:11]3[CH2:16][C@H:15]([OH:17])[C@@H:14]([CH2:18][OH:19])[O:13][CH2:12]3)[C:9]=2[N:10]=[C:2]1[NH2:1]

Participants

4

Reactant 2

HCID 60961AdenosineHCID 21765604HCID 21765604, compound

Product 1

HCID 135450943HCID 135450943, compound

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A mixture of 145 mg (0.48 mmol) of compound 12 and 0.5 ml of a suspension of adenosine deaminase in 100 ml 0.05 M phosphate buffer, pH 7.5, was incubated for 4 hours at 30° C. The reaction mixture was concentrated to about 15 ml and the precipitate filtered off. Recrystallization from water provided 50 mg analytically pure compound 13. The filtrates were placed onto an XAD column (25×2 cm), which was eluted with water followed by MeOH-water (3:1). Evaporation gave an extra 70 mg of compound 13 as a white product to a total of 0.43 mmol (89%). mp >300° C.

Workup

  1. concentrationThe reaction mixture was concentrated to about 15 ml
  2. filtrationthe precipitate filtered off
  3. customRecrystallization from water

Sources & evidence

ORD record
ord-72b6bcffd21c4c71ab475394cf5fe0fc
Source dataset
uspto-grants-1997_03
Patent number
US05607922

Reaction notes

Loading…