Tetrahydrofuran → HCID 178472984, compound

HRID 2233787Notes

Reaction equation

HRID 2233787 reaction equation
C1COCC1.C([O:9][CH:10]([CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=[O:42])[C:23](=[C:33]2[NH:37][C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[NH:34]2)[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)=[O:25])[CH:17]=1)[OH:15])[CH:11]([OH:13])[CH3:12])(=O)C.[OH-].[Na+].[Cl-].[NH4+]>CO>[NH:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[NH:37][C:33]1=[C:23]([C:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH:14]([OH:15])[CH:10]([OH:9])[CH:11]([OH:13])[CH3:12])[CH:17]=1)=[O:42])[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=1)=[O:25]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 178476317HCID 178476317, compound

Product 1

HCID 178472984HCID 178472984, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 10 ml portion of THF solution containing 104 mg of 1-[{3-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]phenyl}(hydroxy)methyl]-2-hydroxypropyl acetate and 2 ml of methanol solution were mixed with 0.62 ml of 1.0 M sodium hydroxide and stirred for 30 minutes. This was mixed with appropriate amounts of saturated ammonium chloride aqueous solution and purified water, extracted with ethyl acetate and dried with anhydrous magnesium sulfate. After concentration, the thus formed residue was purified by a silica gel column chromatography to obtain 35 mg (37%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-[3-(1,2,3-trihydroxybutyl)phenyl]propane-1,3-dione (Example 9-1) from a hexane-ethyl acetate (1:1-1:3) eluate.

Workup

  1. custompurified water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationAfter concentration
  5. customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-280bbf4fae424d208de1c11cee70cfee
Source dataset
uspto-grants-2010_05
Patent number
US07709519B2

Reaction notes

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