Water → HCID 86634371, compound

HRID 1191272Notes

Reaction equation

HRID 1191272 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@@H:9]([O:10]C(C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:8][CH2:7][N:6]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N+:2]=[N-:3].C(=O)([O-])[O-].[K+].[K+].O>CO>[N:1]([CH2:4][C@@H:5]1[C@H:9]([OH:10])[CH2:8][CH2:7][N:6]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86634369HCID 86634369, compound

Product 1

HCID 86634371HCID 86634371, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound 4 (1.22 g) in methanol (20 mL), potassium carbonate (0.91 g) was added. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was added water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→4:1→3:1) to obtain the title compound (0.66 g) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→4:1→3:1)

Sources & evidence

ORD record
ord-ce93e428ced8446e9bab0f12e376acd0
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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