Diiodomethane → Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

HRID 895099

Reaction equation

HRID 895099 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22](N)=[N:23][C:24]=2[Cl:28])(=[O:3])[CH3:2].[I:30]CI.N(OCCCCC)=O>C(#N)C>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][C:16](=[O:18])[CH3:17])[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([I:30])=[N:23][C:24]=2[Cl:28])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 10026Pentyl nitriteHCID 10788628(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2-amino-6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

Product 1

HCID 482588Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(2-amino-6-chloropurin-9-yl)oxolan-3-yl acetate in acetonitrile was added diiodomethane and n-pentyl nitrite. The mixture was heated under nitrogen for 20 hours, then solvent removed under reduced pressure. The residue was purified by chromatography on silica gel, eluting with hexanes to hexanes/ethyl acetate 2:1, to provide (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(6-chloro-2-iodopurin-9-yl)oxolan-3-yl acetate, which may be recrystallized from ethanol.

Workup

  1. temperatureThe mixture was heated under nitrogen for 20 hours
  2. customsolvent removed under reduced pressure
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting with hexanes to hexanes/ethyl acetate 2:1

Sources & evidence

ORD record
ord-9ba3d757d3e64f63bac5e5f97322b588
Source dataset
uspto-grants-2005_07
Patent number
US06914053B2

Linked notes

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