(2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-chloro-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-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

HRID 1293057Notes

Reaction equation

HRID 1293057 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][NH2:10])=[CH:4][CH:3]=1.[C:18]([O:26][C@@H:27]1[C@H:31]([O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:30]([C:41]([NH:43][CH2:44][CH3:45])=[O:42])[O:29][C@H:28]1[N:46]1[CH:54]=[N:53][C:52]2[C:47]1=[N:48][C:49]([I:56])=[N:50][C:51]=2Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)(C)C>[C:18]([O:26][C@@H:27]1[C@H:31]([O:32][C:33](=[O:40])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C@@H:30]([C:41]([NH:43][CH2:44][CH3:45])=[O:42])[O:29][C@H:28]1[N:46]1[CH:54]=[N:53][C:52]2[C:47]1=[N:48][C:49]([I:56])=[N:50][C:51]=2[NH:10][CH2:9][CH:8]([C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 10189909(2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-chloro-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoateHCID 131104422,2-Bis(4-chlorophenyl)ethanamine

Product 1

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 benzoateYield 48.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,2-Bis(4-chlorophenyl)ethanamine (426 mg, 1.51 mmol) (J. Am. Chem. Soc., 1983, 105(10), 3138) was added to a stirred solution of (2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-chloro-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (500 mg, 0.755 mmol) (Preparation 47) in isopropyl alcohol (20 ml) at room temperature. The reaction mixture was stirred at room temperature for 48 hours. The solvent was removed under reduced pressure to give a residue that was purified by column chromatography on silica gel eluting with dichloromethane:methanol:(99:1 by volume). The solvent was removed under reduced pressure to give the title compound (329 mg) as a foam.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give a residue that
  3. customwas purified by column chromatography on silica gel eluting with dichloromethane
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-94fe91b646884d24878017fb046350c5
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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