Potassium Hydroxide → N-(4-iso-propylbenzenesulfonyl)-alpha-(4-carboxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide dipotassium salt

HRID 744188Notes

Reaction equation

HRID 744188 reaction equation
[K:1].[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15](=[O:40])[CH:16]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]C)=[O:25])=[CH:20][C:19]=2[CH2:28][CH2:29][CH3:30])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[OH-].[K+].C(Cl)Cl.CO.[NH4+].[OH-]>CO.O>[K:1].[K:1].[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15](=[O:40])[CH:16]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][C:19]=2[CH2:28][CH2:29][CH3:30])(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 21896990Dichloromethane methanol ammonium hydroxideHCID 86749852N-(4-iso-propylbenzenesulfonyl)-alpha-(4-carbomethoxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide potassium salt

Product 1

HCID 9960645N-(4-iso-propylbenzenesulfonyl)-alpha-(4-carboxy-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide dipotassium saltYield 173.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 204 g (0.345 mol) of the product of Example 6, 420 mL of 1.0N KOH in methanol and 500 mL of water was stirred at 60° C. under a nitrogen atmosphere. After 3 hours TLC analysis (90:10:1 CH2Cl2 -MeOH-NH4OH) indicated that ester hydrolysis was complete. The reaction mixture was cool slightly, then concentrated on a rotary evaporator to a weight of 500 g. 2.5 L of isopropanol was added and the solution reconcentrated to an oil. The residue was flushed with an additional 2-3 L of isopropanol until crystallization began. The slurry was concentrated to ca. 1.5 L and cooled to 30° C., filtered and washed with 300 mL of IPA and 500 mL of ether. The product was dried affording 185 g of semi-pure title compound as a white crystalline solid. A second crop of 17 g was obtained from the filtrate after cooling. The material was recrystallized as follows: 168 g was dissolved in 3 L of absolute ethanol at reflux, filtered hot, and the flask and funnel rinsed with an additional 500 mL of ethanol. 70 mL of water was added and the solution cooled to 0° C. over 2 hr then aged at 0° C. for 6 hr. The product was collected by filtration, washed with ethanol, then air. The yield was 160.8 g of the title compound as a white crystalline solid.

Workup

  1. temperatureThe reaction mixture was cool slightly
  2. concentrationconcentrated on a rotary evaporator to a weight of 500 g
  3. addition2.5 L of isopropanol was added
  4. customThe residue was flushed with an additional 2-3 L of isopropanol until crystallization
  5. concentrationThe slurry was concentrated to ca. 1.5 L
  6. temperaturecooled to 30° C.
  7. filtrationfiltered
  8. washwashed with 300 mL of IPA and 500 mL of ether
  9. customThe product was dried

Sources & evidence

ORD record
ord-42a9cbc144ff4e0382ec10b3c8ad1200
Source dataset
uspto-grants-1996_09
Patent number
US05559135

Reaction notes

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