Sodium Hydroxide → HCID 178525446, compound

HRID 642159Notes

Reaction equation

HRID 642159 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][C:23](=[O:32])[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[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:17]=[CH:18][C:19]([NH:22][C:23](=[O:32])[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:20][CH:21]=1)=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500352HCID 178500352, compound

Product 1

HCID 178525446HCID 178525446, compoundYield 91.8%

Reagents, catalysts & solvents 1

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

Procedure

Into a suspension of methyl 6-[(4-{[2-(5-iodo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazino]carbonyl}phenyl)amino]-6-oxohexanoate (405 mg, 0.74 mmol) in THF/H2O (2/1) (15 mL) was added NaOH (1.0 N, 3.7 mL). The resulting solution was stirred at rt for 2.5 hr and quenched with HCl (5 N, 2 mL). A yellow solid precipitated out. Filtration, washing with water (4×5 mL) and drying under vacuo at 70° C. for 20 hrs gave the title compound as a yellow powder (363 mg, 91%) in 99.0% purity by HPLC (MaxPlot detection between 230 and 400 mn).

Workup

  1. customquenched with HCl (5 N, 2 mL)
  2. customA yellow solid precipitated out
  3. filtrationFiltration
  4. washwashing with water (4×5 mL)
  5. customdrying under vacuo at 70° C. for 20 hrs

Sources & evidence

ORD record
ord-67afbb619e1a4e8eaf252b1055c26a5a
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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