Sodium Carbonate → N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-2-methyl-1-propanesulfonamide

HRID 1700086노트

반응식

HRID 1700086 반응식
C([O:4][C@H:5]1[C@@H:9]([O:10]C(=O)C)[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([CH2:38][NH:39][S:40]([CH2:43][CH:44]([CH3:46])[CH3:45])(=[O:42])=[O:41])=[N:18][C:19]=3[NH:23][CH2:24][CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:7][C@@H:6]1[CH2:47][O:48]C(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[NH3:14].[OH:10][C@@H:9]1[C@H:5]([OH:4])[C@@H:6]([CH2:47][OH:48])[O:7][C@H:8]1[N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][C:17]([CH2:38][NH:39][S:40]([CH2:43][CH:44]([CH3:46])[CH3:45])(=[O:41])=[O:42])=[N:18][C:19]=2[NH:23][CH2:24][CH:25]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 2

HCID 10340Sodium CarbonateHCID 69972041(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy) methyl]-5-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulfonyl)amino]methyl}-9H-purin-9-yl)tetrahydro-3-furanyl acetate

생성물 2

HCID 222AmmoniaHCID 9960269N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-2-methyl-1-propanesulfonamide수율 99.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy) methyl]-5-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulfonyl)amino]methyl}-9H-purin-9-yl)tetrahydro-3-furanyl acetate (188 mg, 0.26 mmol) (Preparation 9) and sodium carbonate (140 mg, 1.32 mmol) in a mixture of water (2 ml) and methanol (10 ml) was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic phase was separated and the solvent removed under reduced pressure. The residue was then purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:0.88 ammonia (95:5:0.5 by volume) gradually changing to dichloromethane:methanol:0.88 ammonia (90:10:1 by volume) to afford the title compound (77 mg).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. customThe organic phase was separated
  4. customthe solvent removed under reduced pressure
  5. customThe residue was then purified by column chromatography on silica gel eluting with a gradient system of dichloromethane

출처 및 근거

ORD 기록
ord-8846c666b85745a8b719f1a597c2de03
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350735B1

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