Hydrochloric Acid → HCID 57720190, compound

HRID 1985842Notes

Reaction equation

HRID 1985842 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][C:33]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:11][NH:12][C:13]1[N:17]([C@@H:18]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]=2[N:14]=1)=O)C.[BH4-].[Na+].Cl>CO>[OH:3][CH2:4][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][C:33]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:11][NH:12][C:13]1[N:17]([C@@H:18]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]=2[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57720302HCID 57720302, compound

Product 1

HCID 57720190HCID 57720190, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Ethoxycarbonylmethyloxy-4-phenylbenzylamino)-1-(β-D-ribofuranosyl)-1H-benzimidazole (53 mg) was dissolved in methanol (5 mL). To the mixture was added sodium tetrahydroborate (8 mg), and the mixture was stirred at room temperature for 1 hours. To the reaction mixture was added 1 mol/L hydrochloric acid (0.5 mL), and the solvent was removed 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 (21 mg).

Workup

  1. customthe solvent was removed under reduced pressure
  2. 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-63539ca50b9b43ce81147949ef9421f6
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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