(2R,3R,4S,5S)-4-(Benzoyloxy)-2-(6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate → (2R,3R,4S,5S)-4-(Benzoyloxy)-2-(6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-2-cyano-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

HRID 1293058Notes

Reaction equation

HRID 1293058 reaction equation
[Cu][C:2]#[N:3].[C:4]([O:12][C@@H:13]1[C@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:16]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])[O:15][C@H:14]1[N:32]1[CH:40]=[N:39][C:38]2[C:33]1=[N:34][C:35](I)=[N:36][C:37]=2[NH:41][CH2:42][CH:43]([C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=1)[C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>O>[C:4]([O:12][C@@H:13]1[C@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@@H:16]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])[O:15][C@H:14]1[N:32]1[CH:40]=[N:39][C:38]2[C:33]1=[N:34][C:35]([C:2]#[N:3])=[N:36][C:37]=2[NH:41][CH2:42][CH:43]([C:44]1[CH:45]=[CH:46][C:47]([Cl:50])=[CH:48][CH:49]=1)[C:51]1[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 60018579(2R,3R,4S,5S)-4-(Benzoyloxy)-2-(6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 60018584(2R,3R,4S,5S)-4-(Benzoyloxy)-2-(6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-2-cyano-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Copper(I) cyanide was added to a solution of (2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (440 mg, 0.494 mmol) (Preparation 67) in N′N′-dimethylformamide (10 ml). The reaction mixture was stirred at 90° C. overnight. The reaction mixture was poured into water (15 ml). The precipitate was filtered off and stirred in dichloromethane (50 ml) for 10 minutes. The dichloromethane was filtered, dried over anhydrous magnesium sulphate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (98: 2 by volume). The solvent was removed under reduced pressure to give the title compound (227 mg) as a foam.

Workup

  1. filtrationThe precipitate was filtered off
  2. stirringstirred in dichloromethane (50 ml) for 10 minutes
  3. filtrationThe dichloromethane was filtered
  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:methanol (98: 2 by volume)
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-704daae507a04285898e8fd271317315
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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