Sodium Hydroxide → N-[3,5-Dichloro-4-(4-hydroxy-3-nonylcarbamoyl-phenoxy)-phenyl]-malonamic acid

HRID 584016Notes

Reaction equation

HRID 584016 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([C:23](=[O:34])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:17]=2)=[C:10]([Cl:35])[CH:9]=1)=[O:6].[OH-].[Na+]>CO.O.[OH-].[K+]>[Cl:14][C:12]1[CH:13]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][C:3]([OH:36])=[O:2])[CH:9]=[C:10]([Cl:35])[C:11]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([C:23](=[O:34])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:17]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 12114185N-[3,5-Dichloro-4-(4-hydroxy-3-nonylcarbamoyl-phenoxy)-phenyl]-malonamic acid methyl ester

Product 1

HCID 12114186N-[3,5-Dichloro-4-(4-hydroxy-3-nonylcarbamoyl-phenoxy)-phenyl]-malonamic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

N-[3,5-Dichloro-4-(4-hydroxy-3-nonylcarbamoyl-phenoxy)-phenyl]-malonamic acid methyl ester (78 mg, 0.14 mmol) was dissolved in a mixture of MeOH (2 ml), water (1.5 ml), and 1 M NaOH (0.5 ml, 0.5 mmol). The resulting solution was stirred at RT for 2 h then diluted with 15 ml 0.1 M KOH. The solution was washed with a 1:1 mixture of Et2O and EtOAc (3×10 ml) and the combined organic washings were extracted with 0.1 M KOH (2×10 ml). The combined basic solutions were acidified with concentrated HCl and extracted with EtOAc (3×15 ml) and the combined organic extracts washed with brine. The dried extracts were filtered and concentrated to give the title compound of Step G and Example 3, (64 mg). MS (APCl+) Calc.: 524.1. Found: 525.1 (M+).

Workup

  1. washThe solution was washed with a 1:1 mixture of Et2O and EtOAc (3×10 ml)
  2. extractionthe combined organic washings were extracted with 0.1 M KOH (2×10 ml)
  3. extractionextracted with EtOAc (3×15 ml)
  4. washthe combined organic extracts washed with brine
  5. filtrationThe dried extracts were filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6996e6595104c81b4ecfeeacad47c93
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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