Ammonia → (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol

HRID 1293028노트

반응식

HRID 1293028 반응식
N.C([O:5][C@H:6]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([C:39]#[N:40])=[N:19][C:20]=3[NH:24][CH2:25][CH:26]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:8][C@@H:7]1[CH2:41][O:42]C(=O)C)(=O)C>C(O)C.[Pd]>[NH2:40][CH2:39][C:18]1[N:17]=[C:16]2[C:21]([N:22]=[CH:23][N:15]2[C@H:9]2[C@H:10]([OH:11])[C@H:6]([OH:5])[C@@H:7]([CH2:41][OH:42])[O:8]2)=[C:20]([NH:24][CH2:25][CH:26]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:19]=1

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 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

생성물 1

HCID 60018582(2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol수율 37.7%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

Ammonia gas was passed through an ice cold solution of (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 (1.2 g, 2 mmol) (Preparation 71) in ethanol (40 ml) until the solution was saturated. 10% Palladium on carbon (120 mg) was added and the reaction mixture was stirred under an atmosphere of hydrogen gas (413.7 kPa, 60 psi) at room temperature for 40 hours. The suspension was filtered through Arbocel (Trade Mark) and the solvent was removed from the filtrate under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (96:4:0.4 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (94:6:0.5 by volume). The solvent was removed under reduced pressure to give the title compound (358 mg) as a foam.

후처리

  1. filtrationThe suspension was filtered through Arbocel (Trade Mark)
  2. customthe solvent was removed from the filtrate under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:0.88 concentrated aqueous ammonia (96:4:0.4 by volume) increasing in polarity to dichloromethane
  5. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-f292a6f2b0444927896c5e3d86817f07
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238676B2

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