(2R,3R,4S,5S)-4-(Benzoyloxy)-2-(2-cyano-6-[(1-naphthylmethyl)amino]-9H-purin-9-yl}-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate → (2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(1-naphthylmethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

HRID 1293059ノート

反応式

HRID 1293059 の反応式
C([O:9][C@@H:10]1[C@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@@H:13]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[O:12][C@H:11]1[N:29]1[CH:37]=[N:36][C:35]2[C:30]1=[N:31][C:32]([C:50]#[N:51])=[N:33][C:34]=2[NH:38][CH2:39][C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][CH:41]=1)(=O)C1C=CC=CC=1>[Pd].N.C(O)C>[NH2:51][CH2:50][C:32]1[N:31]=[C:30]2[C:35]([N:36]=[CH:37][N:29]2[C@@H:11]2[O:12][C@H:13]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])[C@@H:14]([OH:15])[C@H:10]2[OH:9])=[C:34]([NH:38][CH2:39][C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH:43]=[CH:42][CH:41]=2)[N:33]=1

参加物

5

反応物 1

HCID 60018577(2R,3R,4S,5S)-4-(Benzoyloxy)-2-(2-cyano-6-[(1-naphthylmethyl)amino]-9H-purin-9-yl}-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

生成物 1

HCID 20816799(2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(1-naphthylmethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide収率 70.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 222Ammonia溶媒HCID 702Ethanol溶媒

実験手順

10% Palladium on carbon was added to a solution of (2R,3R,4S,5S)-4-(benzoyloxy)-2-{2-cyano-6-[(1-naphthylmethyl)amino]-9H-purin-9-yl}-5-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (487 mg, 0.71 mmol) (Preparation 70) dissolved in a saturated solution of ammonia in ethanol. The reaction mixture was stirred for 16 hours under an atmosphere of hydrogen gas (414 kPa, 60 psi). The reaction mixture was then filtered through Arbocel (Trade Mark) and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (80:20:2 by volume). The solvent was removed under reduced pressure to give the title compound (240 mg) as a foam.

後処理

  1. filtrationThe reaction mixture was then filtered through Arbocel (Trade Mark)
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane
  5. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-3adab0b8e2fa4978a4bdb59b497a2a08
出典データセット
uspto-grants-2007_07
特許番号
US07238676B2

反応ノート

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