(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 1293059노트

반응식

HRID 1293059 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 222Ammonia용매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3adab0b8e2fa4978a4bdb59b497a2a08
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238676B2

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