Sodium Hydroxide → HCID 178525328, compound

HRID 642173Notes

Reaction equation

HRID 642173 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:12][NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36]C)=[O:35])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:18][CH:17]=1)=[O:15].[OH-].[Na+]>C1COCC1.O>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:12][NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:18][CH:17]=1)=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178499990HCID 178499990, compound

Product 1

HCID 178525328HCID 178525328, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Into a suspension of methyl 3-(4-{[(4-{[2-(5-iodo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazino]carbonyl}phenyl)amino]sulfonyl}phenyl)propanoate (166 mg, 0.26 mmol) in THF/H2O (2/1) (6 mL) was added NaOH (1.0 N, 1.3 mL). The resulting solution was stirred at rt for 1 hr and quenched with HCl (5 N, 1.3 mL). A yellow solid precipitated out. Filtration, washing with water (4×2 mL) and drying under vacuo at 60° C. for 18 hrs gave the title compound as a yellow powder (133 mg, 81%) in 99.3% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customquenched with HCl (5 N, 1.3 mL)
  2. customA yellow solid precipitated out
  3. filtrationFiltration
  4. washwashing with water (4×2 mL)
  5. customdrying under vacuo at 60° C. for 18 hrs

Sources & evidence

ORD record
ord-cf2e90bd58aa411791cc05cff1a2c094
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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