Hydrochloric Acid → HCID 54435224、化合物

HRID 434266ノート

反応式

HRID 434266 の反応式
[CH2:1]([O:8][C@:9]1([CH:37]=[CH2:38])[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:12][C@@H:11]([N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[C@@H:10]1[O:32]S(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Na+].Cl>C(O)C>[CH2:1]([O:8][C@:9]1([CH:37]=[CH2:38])[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:12][C@@H:11]([N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[C@H:10]1[OH:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15332425HCID 15332425、化合物

生成物 1

HCID 54435224HCID 54435224、化合物収率 74.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of nucleoside 25 (2.53 g, 4.66 mmol) in a mixture of ethanol (50 cm3), water (50 cm3) and 1 M aqueous sodium hydroxide (15 cm3) was stirred under reflux for 16 h. The mixture was neutralised using dilute aqueous hydrochloric acid, the solvent was evaporated under reduced pressure, and the residue was extracted with dichloromethane (3×120 cm3). The combined extract was washed with saturated aqueous sodium hydrogencarbonate (3×150 cm3) and dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (99:1) as eluent to give 26 as a white foam (1.61 g, 74%). δH (CDCl3) 9.89 (1H, br s, NH), 7.50 (1H, d, J 1.1, 6-H), 7.41-7.26 (Bn), 6.28 (1H, d, J 2.8, 1′-H), 6.05 (1H, dd, J 11.1, 17.9, 1″-H), 5.58-5.50 (2H, m, 2″-Ha, 2″-Hb), 4.98 (1H, d, J 9.0, 2′-OH), 4.64-4.31 (6H, m, 2′-H, 4′-H, Bn), 3.73 (2H, m, 5′-Ha, 5′-Hb), 1.73 (1H, d, J 0.6, CH3). δC (CDCl3) 165.1 (C-4), 150.5 (C-2), 138.4, 138.0, 136.7 (C-6, Bn), 130.4 (C-1″), 128.8, 128.6, 128.5, 128.1, 128.0, 127.8 (Bn), 120.6 (C-2″), 108.1 (C-5), 88.6 (C-1′), 87.9 (C-3′), 87.2 (C-4′), 73.7 (C-2′), 71.8 (C-5′), 69.7, 66.3 (Bn), 12.3 (CH3). Found: C, 66.8; H, 6.2; N, 5.9; C26H28N2O8 requires C, 67.2; H, 6.1; N, 6.0.

後処理

  1. temperatureunder reflux for 16 h
  2. customthe solvent was evaporated under reduced pressure
  3. extractionthe residue was extracted with dichloromethane (3×120 cm3)
  4. extractionThe combined extract
  5. washwas washed with saturated aqueous sodium hydrogencarbonate (3×150 cm3)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-ddb80f01264c43f8955147a11ffc82ab
出典データセット
uspto-grants-2003_12
特許番号
US06670461B1

反応ノート

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