Triethylamine → (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

HRID 897123Notes

Reaction equation

HRID 897123 reaction equation
C(N(CC)CC)C.[C:8]([O:11][C@H:12]1[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([N:21]2[CH:29]=[N:28][C:27]3[C:22]2=[N:23][C:24]([C:31]#[N:32])=[N:25][C:26]=3Cl)[O:14][C@@H:13]1[CH2:33][O:34][C:35](=[O:37])[CH3:36])(=[O:10])[CH3:9].[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]([C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=2)[CH2:46][NH2:47])=[CH:41][CH:40]=1>C(#N)C>[C:8]([O:11][C@H:12]1[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([N:21]2[CH:29]=[N:28][C:27]3[C:22]2=[N:23][C:24]([C:31]#[N:32])=[N:25][C:26]=3[NH:47][CH2:46][CH:45]([C:42]2[CH:43]=[CH:44][C:39]([Cl:38])=[CH:40][CH:41]=2)[C:48]2[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=2)[O:14][C@@H:13]1[CH2:33][O:34][C:35](=[O:37])[CH3:36])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 131104422,2-Bis(4-chlorophenyl)ethanamineHCID 22948625(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Product 1

HCID 60018583(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetateYield 91.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (0.2 ml, 1.14 mmol) was added to a stirred solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate (500 mg, 1.14 mmol) (Preparation 45) and 2,2-bis(4-chlorophenyl)ethanamine (919 mg, 1.2 mmol) (J. Am. Chem. Soc., 1983, 105 (10), 3138) in acetonitrile (5 ml) at room temperature. The reaction mixture was stirred for 16 hours. The solvent was then removed under reduced pressure and the residue was dissolved in dichloromethane (20 ml). The solution was washed with water (10 ml) and saturated sodium chloride solution (10 ml), dried over anhydrous magnesium sulphate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:(99:1 by volume) increasing in polarity to dichloromethane:methanol (98.5:1.5 by volume). The solvent was removed under reduced pressure to give the title compound (698 mg) as a foam.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (20 ml)
  3. washThe solution was washed with water (10 ml) and saturated sodium chloride solution (10 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  7. temperaturemethanol:(99:1 by volume) increasing in polarity to dichloromethane:methanol (98.5:1.5 by volume)
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5f536bedd7af41e5a48dcd5dc963273f
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

Loading…