Triethylamine → HCID 20792644, compound

HRID 2184261Notes

Reaction equation

HRID 2184261 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([I:24])=[N:18][C:19]=3Cl)[O:7][C@@H:6]1[CH2:25][O:26][C:27](=[O:29])[CH3:28])(=[O:3])[CH3:2].[C:30]1([CH:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:37][NH2:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>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]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([I:24])=[N:18][C:19]=3[NH:38][CH2:37][CH:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:7][C@@H:6]1[CH2:25][O:26][C:27](=[O:29])[CH3:28])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775752,2-DiphenylethylamineHCID 482588Acetic acid (2R,3R,4R,5R)-3,4-diacetoxy-5-(6-chloro-2-iodo-purin-9-YL)-tetrahydro-furan-2-ylmethyl ester

Product 1

HCID 20792644HCID 20792644, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-iodo-9H-purin-9-yl)tetrahydro-3-furanyl acetate (J. Med. Chem., 35, 248, (1992)) (15.2g, 28.2 mmol), 2,2-diphenylethylamine (6.1 g, 30.9 mmol), triethylamine (11.4 g, 112.8 mmol) and acetonitrile (200 ml) was stirred at room temperature, under a nitrogen atmosphere, for 24 hours, followed by heating under reflux for 90 minutes. The solvent was removed under reduced pressure and the residue partitioned between dichloromethane (500 ml) and water (200 ml). The organic phase was separated and the solvent removed under reduced pressure to give the title compound as a pale yellow foam (18.8g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 90 minutes
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between dichloromethane (500 ml) and water (200 ml)
  5. customThe organic phase was separated
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6d9e26c3c2ea4a6dbd5c786789754515
Source dataset
uspto-grants-2005_05
Patent number
US06900309B1

Reaction notes

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