HCID 57720218, compound → HCID 57720313, compound

HRID 1985849Notes

Reaction equation

HRID 1985849 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:40]=[CH:41][CH:42]=1)[CH2:20][NH:21][C:22]1[N:26]([C@@H:27]2[O:33][C@H:32]([CH2:34][OH:35])[C@@H:30]([OH:31])[C@H:28]2[OH:29])[C:25]2[CH:36]=[CH:37][CH:38]=[CH:39][C:24]=2[N:23]=1)=[O:14])=O)(C)(C)C>Cl.C(O)C>[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:40]=[CH:41][CH:42]=1)[CH2:20][NH:21][C:22]1[N:26]([C@@H:27]2[O:33][C@H:32]([CH2:34][OH:35])[C@@H:30]([OH:31])[C@H:28]2[OH:29])[C:25]2[CH:36]=[CH:37][CH:38]=[CH:39][C:24]=2[N:23]=1)=[O:14]

Participants

3

Reactant 1

HCID 57720218HCID 57720218, compound

Product 1

HCID 57720313HCID 57720313, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

2-{3-[(3-t-Butoxycarbonylaminopropylcarbamoyl)methoxy]benzylamino}-1-(β-D-ribofuranosyl)-1H-benzimidazole (15 mg) was dissolved in 22% hydrochloride-ethanol solution, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and 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=90/10-10/90) to give the title compound (9 mg).

Workup

  1. concentrationThe reaction mixture was concentrated 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=90/10-10/90)

Sources & evidence

ORD record
ord-a18eec13e7d440dbafd25f187010e757
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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