Tetrahydrofuran → HCID 178472984, compound

HRID 658113Notes

Reaction equation

HRID 658113 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-0b5901a2314e48e1b257427b5eb36b86
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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