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

HRID 1985847Notes

Reaction equation

HRID 1985847 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2a160b51cd2d41428f309c53e9198168
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

Loading…