Ammonia → 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile

HRID 2268409노트

반응식

HRID 2268409 반응식
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][C:27]([C:48]#[N:49])=[N:28][C:29]=3[NH:33][CH2:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:12][C@@H:11]1[CH2:50][O:51][CH3:52])(=O)C1C=CC=CC=1.N>CO>[OH:15][C@@H:14]1[C@H:10]([OH:9])[C@@H:11]([CH2:50][O:51][CH3:52])[O:12][C@H:13]1[N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][C:27]([C:48]#[N:49])=[N:28][C:29]=2[NH:33][CH2:34][CH:35]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

4

반응물 2

HCID 222AmmoniaHCID 59975289(2R,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

생성물 1

HCID 599753059-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile수율 46.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of (2R,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-(methoxymethyl)tetrahydro-3-furanyl benzoate (preparation 11) (6.75 g, 9.72 mmol) in methanol (300 ml) saturated with ammonia gas was stirred at room temperature for 72 hr. The solvent was removed under reduced pressure, the residue dissolved in dichloromethane and the solvent removed under reduced pressure (repeated). The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2) gradually changing to dichloromethane:methanol (96:4). The residue was triturated with diethyl ether, filtered, washed with diethyl ether and dried to afford the title compound as a solid (2.20 g). MS: 487(MH+).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. customthe solvent removed under reduced pressure (repeated)
  4. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2)
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-dff8ace13ee14e76a0284c4be3f7b7da
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326359B1

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