Methanol → HCID 178520863, compound

HRID 658110Notes

Reaction equation

HRID 658110 reaction equation
CO.[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]1=[C:12]([C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1)=[O:29])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C@@H:21]2[CH2:25][O:24]C(C)(C)[O:22]2)[CH:16]=1)=[O:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>O>[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]1=[C:12]([C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1)=[O:29])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C@@H:21]([OH:22])[CH2:25][OH:24])[CH:16]=1)=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 178431475HCID 178431475, compound

Product 1

HCID 178520863HCID 178520863, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 20 ml portion of methanol solution containing 1.68 g of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-{3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenyl}-3-(3-fluorophenyl)propane-1,3-dione was mixed with 560 mg of p-toluenesulfonic acid monohydrate and stirred at room temperature for 18 hours. This was mixed with appropriate amounts of purified water and saturated sodium bicarbonate aqueous solution, 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 640 mg (42%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-{3-[(1R)-1,2-dihydroxyethyl]phenyl}-3-(3-fluorophenyl)propane-1,3-dione (Example 4-1) from a hexane-ethyl acetate (3:1-1:3) eluate.

Workup

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

Sources & evidence

ORD record
ord-1dc9c4c3a72c4f6b96e926b2b765f3d3
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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