HCID 86756695, compound → (2S,3S,4R,5R)-5-(6-amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolane-2-carboxylic acid

HRID 1977100Notes

Reaction equation

HRID 1977100 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:12]1[C@H:19]2[C@@H:15]([O:16]C(C)(C)[O:18]2)[C@H:14]([C:22]([OH:24])=[O:23])[O:13]1>C(O)=O>[NH2:1][C:2]1[N:10]=[C:9]([I:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:13][C@H:14]([C:22]([OH:24])=[O:23])[C@@H:15]([OH:16])[C@H:19]1[OH:18]

Participants

3

Reactant 1

HCID 86756695HCID 86756695, compound

Product 1

HCID 15667086(2S,3S,4R,5R)-5-(6-amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolane-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1.72 g (3.85 mmol) of (2R,1R,4R,5R)-4-(6-amino-2-iodopurin-9-yl)-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]octane-2-carboxylic acid (6.7) in 80 mL of 50% HCOOH was stirred at 80° C. for 1.5 hours. The reaction mixture was evaporated under reduced pressure, dissolved in H2O, and the solution was evaporated again. This process was repeated until there was no odor of formic acid in the residue. Recrystallization from water yielded 1.33 g (85%) 6.8 as a white solid, m.p. 221-223° C. dec. 1H NMR (300 MHz, DMSO-d6) δ 8.31 (s, 1H, H-8), 7.68 (s, 2H, NH2), 5.90 (d, J=6.55 Hz, 1H, H-1′), 4.42 (m, 1H, H-2′), 4.35 (d, J=2.31 Hz, 1H, H-4′), 4.22 (m, 1H, H-3′).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutiondissolved in H2O
  3. customthe solution was evaporated again
  4. customRecrystallization from water

Sources & evidence

ORD record
ord-a3574cc242c44f28814079feed86ea99
Source dataset
uspto-grants-2001_05
Patent number
US06232297B1

Reaction notes

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