Adenosine → HCID 135412808, compound

HRID 1871240Notes

Reaction equation

HRID 1871240 reaction equation
[F:1][C@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[S:4][CH:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([NH2:20])=[N:14][C:15]=2N.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:23]>Cl>[F:1][C@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[S:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:15](=[O:23])[NH:14][C:13]([NH2:20])=[N:12][C:11]1=2

Participants

4

Reactant 2

HCID 60961AdenosineHCID 15450639HCID 15450639, compound

Product 1

HCID 135412808HCID 135412808, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

114 mg of the crude anomer mixture of 9-(2-deoxy-2-fluoro-4-thio-D-arabinofuranosyl)-2,6-diaminopurine (beta/alpha=1.55) obtained in Synthesis Example 2 was suspended in 25 ml of tris hydrochloric acid buffer solution (pH=7.0). To this suspension was added 0.43 ml (100 units) of adenosine deaminase, and the mixture was stirred at room temperature for 6 hours. The reaction solution was purified by ODS reverse phase column chromatography to obtain 48 mg (yield 48%) of the title compound.

Workup

  1. customobtained in Synthesis Example 2
  2. customThe reaction solution was purified by ODS reverse phase column chromatography

Sources & evidence

ORD record
ord-ae6abeed2d9c498292316fead190f678
Source dataset
uspto-grants-2000_08
Patent number
US06103707

Reaction notes

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