(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 897125

反応式

HRID 897125 の反応式
[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

参加物

4

反応物 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

生成物 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 benzoate収率 48.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-54f104a417c1468a9f9e6ad2519ed5d3
出典データセット
uspto-grants-2005_07
特許番号
US06921753B2

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