Sodium Hydroxide → HCID 178525474, compound

HRID 642170Notes

Reaction equation

HRID 642170 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12]([NH:14][C:15]3[CH:42]=[CH:41][C:18]([C:19]([NH:21][N:22]=[C:23]4[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([I:32])[CH:30]=5)[N:25]([CH2:33][CH2:34][CH2:35][C:36]([O:38]C)=[O:37])[C:24]4=[O:40])=[O:20])=[CH:17][CH:16]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Na+]>C1COCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH:21]/[N:22]=[C:23]4\[C:24](=[O:40])[N:25]([CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])[C:26]5[C:31]\4=[CH:30][C:29]([I:32])=[CH:28][CH:27]=5)=[O:20])=[CH:41][CH:42]=3)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500492HCID 178500492, compound

Product 1

HCID 178525474HCID 178525474, compoundYield 61.2%

Reagents, catalysts & solvents 1

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

Procedure

Into a suspension of methyl 4-{3-[(4-{[3-(1,3-benzodioxol-5-yl)propanoyl]amino}benzoyl)hydrazono]-5-iodo-2-oxo-2,3-dihydro-1H-indol-1-yl}butanoate (150 mg, 0.22 mmol) in THF/H2O (2/1) (10 mL) was added NaOH (1.0 N, 1.1 mL). The resulting solution was stirred at rt for 2 hr and quenched with HCl (5 N, 4 mL). A yellow solid precipitated out. Filtration, washing with water (4×10 mL) and drying under vacuo at 60° C. for 15 hrs gave the title compound as a yellow powder (90 mg, 58%) in 95.5% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. customquenched with HCl (5 N, 4 mL)
  2. customA yellow solid precipitated out
  3. filtrationFiltration
  4. washwashing with water (4×10 mL)
  5. customdrying under vacuo at 60° C. for 15 hrs

Sources & evidence

ORD record
ord-7a260e2b16ba410faf1b9b4161ec434e
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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