Sodium Carbonate → 6-[(2,2-Diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamide

HRID 1168275ノート

反応式

HRID 1168275 の反応式
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([C:45]([NH:47][CH2:48][CH2:49][N:50]1[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]1)=[O:46])=[N:25][C:26]=2[NH:30][CH2:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:33]1([CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:31][NH:30][C:26]2[N:25]=[C:24]([C:45]([NH:47][CH2:48][CH2:49][N:50]3[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]3)=[O:46])[N:23]=[C:22]3[C:27]=2[N:28]=[CH:29][N:21]3[C@H:6]2[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=3)[O:7]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

参加物

5

反応物 2

HCID 10340Sodium CarbonateHCID 70023610(2R,3R,4R,5R)-4-(Acetyloxy)-2-[6-[(2,2-diphenylethyl)amino]-2-({[2-(1-piperidinyl)ethyl]amino}carbonyl)-9H-purin-9-yl]-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate

生成物 1

HCID 590945016-[(2,2-Diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-N-[2-(1-piperidinyl)ethyl]-9H-purine-2-carboxamide収率 76.3%

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-[6-[(2,2-diphenylethyl)amino]-2-({[2-(1-piperidinyl)ethyl]amino}carbonyl)-9H-purin-9-yl]-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (Preparation 27) (230 mg, 0.31 mmol) and sodium carbonate (130 mg, 1.23 mmol) in methanol (15 ml) and water (1.5 ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was partioned between ethyl acetate (50 ml) and water (10 ml). The organic layer was washed with brine (10 ml), dried (anhydrous sodium sulphate) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) gradually changing to dichloromethane:methanol:0.88 concentrated aqueous ammonia (93:7:0.7 by volume). Product containing fractions were evaporated and the resulting solid triturated with ether, filtered and dried to afford the title compound as a white powder (158 mg).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried (anhydrous sodium sulphate)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
  6. additionProduct containing fractions
  7. customwere evaporated
  8. customthe resulting solid triturated with ether
  9. filtrationfiltered
  10. customdried

出典と根拠

ORDレコード
ord-e0da28a2fc224433beca0f87ecd46817
出典データセット
uspto-grants-2003_09
特許番号
US06624158B2

反応ノート

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