Sodium Hydroxide → HCID 178525429, compound

HRID 642158Notes

Reaction equation

HRID 642158 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:34])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[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:34])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:20][CH:21]=1)=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500268HCID 178500268, compound

Product 1

HCID 178525429HCID 178525429, compoundYield 82.8%

Reagents, catalysts & solvents 1

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

Procedure

Into a suspension of methyl 8-[(4-{[2-(5-iodo-2-oxo-1,2-dihydro-3H-indol-3-ylidene)hydrazino]carbonyl}phenyl)amino]-8-oxooctanoate (420 mg, 0.73 mmol) in THF/H2O (2/1) (15 mL) was added NaOH (1.0 N, 3.6 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 (340 mg, 82%) in 99.1% purity by HPLC (MaxPlot detection between 230 and 400 nm).

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-7ec61535d18b46c383f1fc21adce4c92
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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