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 1700086ノート

反応式

HRID 1700086 の反応式
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

参加物

6

反応物 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

生成物 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-propanesulfonamide収率 99.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8846c666b85745a8b719f1a597c2de03
出典データセット
uspto-grants-2002_02
特許番号
US06350735B1

反応ノート

読み込み中…