Ethyl Acetate → HCID 66839268, compound

HRID 546658Notes

Reaction equation

HRID 546658 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](/[CH:26]=[CH:27]/[C:28]2[N:44]=[C:31]3[CH:32]([C:36]4[CH:41]=[CH:40][C:39]([S:42][CH3:43])=[CH:38][CH:37]=4)[CH2:33][CH2:34][CH2:35][N:30]3[N:29]=2)[CH:17]=[CH:18][C:19]=1[N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1.C(OCC)(=O)C.[Cl-].[Na+].[OH2:53]>C(Cl)(Cl)Cl>[CH3:43][S:42]([C:39]1[CH:38]=[CH:37][C:36]([CH:32]2[CH2:33][CH2:34][CH2:35][N:30]3[N:29]=[C:28](/[CH:27]=[CH:26]/[C:16]4[CH:17]=[CH:18][C:19]([N:20]5[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]5)=[C:14]([O:13][CH3:12])[CH:15]=4)[N:44]=[C:31]23)=[CH:41][CH:40]=1)(=[O:9])=[O:53]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 57417360Sodium chloride; waterHCID 66839199HCID 66839199, compound

Product 1

HCID 66839268HCID 66839268, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (6.83 mg) was added to a solution of (−)-(2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(4-methylsulfanylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine obtained in Example 7 (4.5 mg) in chloroform (1 mL), and the reaction solution was stirred at room temperature for one hour. Brine and ethyl acetate were added to the reaction solution and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=9:1) to obtain 0.44 mg of the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: ethyl acetate→ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-dda1a1cb269f4a4b9cd466b119579434
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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