Sodium Hydroxide → HCID 22861437, compound

HRID 440997Notes

Reaction equation

HRID 440997 reaction equation
[N+](C1C=CC(C([O:10][CH2:11][C@H:12]2[O:16][C:15](=[O:17])[N:14]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C@H:13]2[CH3:26])=O)=CC=1)([O-])=O.[OH-].[Na+]>CO>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([N:14]2[C@@H:13]([CH3:26])[C@@H:12]([CH2:11][OH:10])[O:16][C:15]2=[O:17])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57080354HCID 57080354, compound

Product 1

HCID 22861437HCID 22861437, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2.43 g of Compound [76], which had been obtained in Referential Example 6, in 20 ml of methanol, 3.8 ml of an 8% aqueous solution of sodium hydroxide were added, followed by stirring at 50° C. for 20 hours. The reaction mixture was concentrated under reduced pressure. The residue so obtained was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, The residue was purified by subjecting same to chromatography on a silica gel column using gradient elution with hexane-ethyl acetate, whereby 1.04 g of the title compound were obtained (yield: 70%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue so obtained
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified
  9. washelution with hexane-ethyl acetate

Sources & evidence

ORD record
ord-2fd9368120fc4810be1e52de5d19ab93
Source dataset
uspto-grants-1996_05
Patent number
US05521202

Reaction notes

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