Sodium Hydroxide → HCID 69802538, compound

HRID 2414606Notes

Reaction equation

HRID 2414606 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH:17]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:24][CH:23]=2)[C:18]([O:20]C)=[O:19])[CH3:16])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH:17]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:26][CH:27]=2)[C:18]([OH:20])=[O:19])[CH3:16])(=[O:13])=[O:14])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86587122HCID 86587122, compound

Product 1

HCID 69802538HCID 69802538, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl [{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino}(4-{3-[(ethoxycarbonyl)amino]propoxy]phenyl)acetate (0.45 g, 0.85 mmol) and 1N NaOH (4.2 ml, 4.23 mmol) in THF (5 ml) and methanol (5 ml) was stirred at room temperature for 2 h. After removing the solvent, the residue was dissolved in water, neutralized with HCl to pH˜5-6 and extracted with dichloromethane. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to provide 0.36 g of [{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)-amino}(4-{3-[(ethoxycarbonyl)amino]propoxy]phenyl)acetic acid as a solid. Yield 81.8%. Electrospray Mass Spec 519.1 (M+H)+.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d81a11aa4bca4047b156eaca13c94784
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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