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

HRID 897129
ノート
印刷プレビュー

反応式

HRID 897129 の反応式
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].[CH:38]1[C:50]2[CH:49]([CH2:51][NH2:52])[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]=2[CH:41]=[CH:40][CH:39]=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:52][CH2:51][CH:49]2[C:50]3[CH:38]=[CH:39][CH:40]=[CH:41][C:42]=3[C:43]3[C:48]2=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:14][C@@H:13]1[CH2:33][O:34][C:35](=[O:37])[CH3:36])(=[O:10])[CH3:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 14555239(9H-Fluoren-9-yl)methanamineHCID 22948625(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

生成物 1

HCID 60018587(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-{2-cyano-6-[(9H-fluoren-9-ylmethyl) amino]-9H-purin-9-yl}tetrahydro-3-furanyl acetate収率 89.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Triethylamine (0.38 ml, 2.7 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 (1.0 g, 2.3 mmol) (Preparation 45) and 9H-fluoren-9-ylmethanamine (0.49 g, 2.5 mmol) (J. Org. Chem., 1971, 36(23), 3539) in acetonitrile (30 ml) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure. The residue was partially redissolved in ethyl acetate (30 ml). The ethyl acetate was washed with water (11 ml) and a saturated aqueous sodium chloride solution (10 ml). The organic phase was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:ethyl acetate (96:4 by volume) increasing in polarity to dichloromethane:ethyl acetate (94:6 by volume). The solvent was removed under reduced pressure to give the title compound (1.23 g) as a foam.

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was partially redissolved in ethyl acetate (30 ml)
  3. washThe ethyl acetate was washed with water (11 ml)
  4. customThe organic phase was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane:ethyl acetate (96:4 by volume)
  6. temperatureincreasing in polarity to dichloromethane:ethyl acetate (94:6 by volume)
  7. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-daded98932fc47fdb8190616a4b7c3da
出典データセット
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06921753B2

反応ノート

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