Hydrochloric Acid → HCID 69202283, compound

HRID 2220664Notes

Reaction equation

HRID 2220664 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]CC)=[O:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH3:27])(=O)=O.[NH2:28][CH2:29][C@@H:30]([OH:43])[CH2:31][O:32][C:33]1[C:41]2[NH:40][C:39](=[O:42])[NH:38][C:37]=2[CH:36]=[CH:35][CH:34]=1.[OH-].[Na+].Cl>C(O)C>[OH:43][C@@H:30]([CH2:31][O:32][C:33]1[C:41]2[NH:40][C:39](=[O:42])[NH:38][C:37]=2[CH:36]=[CH:35][CH:34]=1)[CH2:29][NH:28][CH2:6][CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23134291HCID 23134291, compoundHCID 69202542HCID 69202542, compound

Product 1

HCID 69202283HCID 69202283, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4′-(2-methanesulfonyloxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate (0.10 g) and 4-((R)-3-amino-2-hydroxypropoxy)-1,3-dihydrobenzimidazol-2-one (0.057 g) in ethanol (2 mL) was stirred at 80° C. overnight. After being cooled to room temperature, a 2 mol/L aqueous solution of sodium hydroxide (0.5 mL) was added to the reaction mixture, and the mixture was stirred at 70° C. for 3 hrs. After being cooled to room temperature, to the mixture was added 2 mol/L hydrochloric acid (0.5 mL). The precipitated insoluble materials were collected by filtration, and purified by preparative reverse phase column chromatography (Shiseido Capcell Pak C18 ODS, 5 μm, 20×50 mm, linear gradient 0.1% aqueous formic acid/acetonitrile=90/10-60/40) to afford the title compound (0.027 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. stirringthe mixture was stirred at 70° C. for 3 hrs
  3. temperatureAfter being cooled to room temperature, to the mixture
  4. filtrationThe precipitated insoluble materials were collected by filtration
  5. custompurified by preparative reverse phase column chromatography (Shiseido Capcell Pak C18 ODS, 5 μm, 20×50 mm, linear gradient 0.1% aqueous formic acid/acetonitrile=90/10-60/40)

Sources & evidence

ORD record
ord-7f535b449f93445b924cfdf3609c10cd
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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