Water → 2-[3-(4-Hydroxybutoxy)-5-phenylbenzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole

HRID 1985847ノート

反応式

HRID 1985847 の反応式
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1.C([O:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]1[CH:39]=[C:40]([CH:43]=[C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:45]=1)[CH:41]=O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>O1CCCC1>[OH:32][CH2:33][CH2:34][CH2:35][CH2:36][O:37][C:38]1[CH:39]=[C:40]([CH:43]=[C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:45]=1)[CH2:41][NH:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[N:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 231438513-(4-Acetoxybutoxy)-5-phenylbenzaldehydeHCID 688410382-Amino-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-benzimidazole

生成物 1

HCID 577201572-[3-(4-Hydroxybutoxy)-5-phenylbenzylamino]-1-(beta-D-ribofuranosyl)-1H-benzimidazole収率 30.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-Amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-benzimidazole (0.20 g) and 3-(4-acetoxybutoxy)-5-phenylbenzaldehyde (0.19 g) were suspended in tetrahydrofuran (3 mL), and the mixture was stirred at room temperature for 13 hours. To the reaction mixture was added sodium triacetoxyborohydride (0.21 g), and the mixture was stirred at room temperature for 24 hours. After adding water to the reaction mixture, the mixture was concentrated under reduced pressure. The obtained residue was dissolved in methanol (2 mL). To the reaction mixture was added 5 mol/L aqueous sodium hydroxide solution (0.5 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added acetic acid (1 mL), and the mixture was concentrated under reduced pressure. The obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90) to give the title compound (0.08 g).

後処理

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in methanol (2 mL)
  4. additionTo the reaction mixture was added 5 mol/L aqueous sodium hydroxide solution (0.5 mL)
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. additionTo the reaction mixture was added acetic acid (1 mL)
  7. concentrationthe mixture was concentrated under reduced pressure
  8. customThe obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90)

出典と根拠

ORDレコード
ord-2a160b51cd2d41428f309c53e9198168
出典データセット
uspto-grants-2009_06
特許番号
US07547680B2

反応ノート

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