Adenosine → HCID 136395584, compound

HRID 130572Notes

Reaction equation

HRID 130572 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[O:19][CH2:18][C@@H:16]([OH:17])[C@@H:14]([OH:15])[C@:12]2([F:20])[OH:13])=[C:4](N)[N:3]=1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:24]>C(O)C(N)(CO)CO.Cl>[F:20][C@:12]1([OH:13])[C@H:14]([OH:15])[C@H:16]([OH:17])[CH2:18][O:19][C@H:11]1[N:8]1[CH:7]=[N:6][C:5]2[C:4](=[O:24])[NH:3][C:2]([NH2:1])=[N:10][C:9]1=2

Participants

4

Reactant 2

HCID 60961AdenosineHCID 86613020HCID 86613020, compound

Product 1

HCID 136395584HCID 136395584, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 93573Tromethamine hydrochlorideSolvent

Procedure

2,6-Diamino-9-(2-fluoro-β-D-arabinosyl)purine (61.2 mg, 0.21 mmol) was dissolved in 50 mM Tris-HCl buffer solution (20 mL, pH 7.0), and adenosine deaminase (71 units) was added to the resultant solution, followed by stirring at room temperature for 1.5 hours. The resultant reaction mixture was subjected to filtration by use of a membrane filter (PTFE, 0.5 μm), and the filtrate was prepared into 60 mL of an aqueous solution. The aqueous solution was purified by means of reverse-phase ODS column chromatography (80 mL, 0 to 2% aqueous acetonitrile), to thereby yield 60.4 mg of the title compound as colorless crystals (yield: 100%).

Workup

  1. customThe resultant reaction mixture
  2. filtrationwas subjected to filtration by use of a membrane
  3. filtrationfilter (PTFE, 0.5 μm)
  4. customthe filtrate was prepared into 60 mL of an aqueous solution
  5. customThe aqueous solution was purified by means of reverse-phase ODS column chromatography (80 mL, 0 to 2% aqueous acetonitrile)

Sources & evidence

ORD record
ord-a0e43271504b45deb4ae94f6ab76b361
Source dataset
uspto-grants-2008_06
Patent number
US07381820B2

Reaction notes

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