Sodium Hydroxide → HCID 131721269, compound

HRID 1075668Notes

Reaction equation

HRID 1075668 reaction equation
C[O:2][C:3](=[O:33])[C@H:4]([CH3:32])[NH:5][C:6](=[O:31])[CH:7]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:20]=[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]2=[O:30])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)[CH3:8].[OH-].[Na+:35]>C1COCC1>[Na+:35].[NH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21](=[CH:20][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH:7]([CH3:8])[C:6]([NH:5][C@H:4]([C:3]([O-:33])=[O:2])[CH3:32])=[O:31])=[C:19]3[C:14]=2[CH:15]=[CH:16][CH:17]=[N:18]3)[C:22]1=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86754073HCID 86754073, compound

Product 1

HCID 131721269HCID 131721269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-{2-[5-(2-oxindol-3-ylidenemethyl)quinol-8-yloxy]propionyl} alanine methyl ester (50 mg, 0.11 mmol) in THF (10 ml) was added dropwise 2N sodium hydroxide (0.1 ml) at 0-50° C. After 4h stirring at room temperature THF (100 ml) was added, the organic layer washed 3 times with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under vacuum. The residue was taken up in 5% sodium bicarbonate (10 ml) and chromatographed on a LoBar RP18 column using as eluant water/methanol (7:3) to give pure title compound in 84-yield (42 mg).

Workup

  1. additionwas added
  2. washthe organic layer washed 3 times with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customchromatographed on a LoBar RP18 column

Sources & evidence

ORD record
ord-cfa5ab080d374ae3b65eeba099ad32cd
Source dataset
uspto-grants-1999_05
Patent number
US05905149

Reaction notes

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