Hydrochloric Acid → alpha-(4-(N-methylcarbamyl)aminosulfonyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetic acid

HRID 1378872Notes

Reaction equation

HRID 1378872 reaction equation
[CH3:1][NH:2][C:3]([NH:5][S:6]([C:9]1[CH:29]=[CH:28][C:12]([O:13][CH:14]([C:19]2[CH:24]=[CH:23][C:22]3[O:25][CH2:26][O:27][C:21]=3[CH:20]=2)[C:15]([O:17]C)=[O:16])=[C:11]([CH2:30][CH2:31][CH3:32])[CH:10]=1)(=[O:8])=[O:7])=[O:4].[OH-].[Na+].C(Cl)(Cl)Cl.CO.C(O)(=O)C.Cl>CO.O>[CH3:1][NH:2][C:3]([NH:5][S:6]([C:9]1[CH:29]=[CH:28][C:12]([O:13][CH:14]([C:19]2[CH:24]=[CH:23][C:22]3[O:25][CH2:26][O:27][C:21]=3[CH:20]=2)[C:15]([OH:17])=[O:16])=[C:11]([CH2:30][CH2:31][CH3:32])[CH:10]=1)(=[O:7])=[O:8])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21866353chloroform methanol HOAcHCID 53963621methyl alpha-(4-(N-methylcarbamyl)aminosulfonyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate

Product 1

HCID 53812605alpha-(4-(N-methylcarbamyl)aminosulfonyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetic acidYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 570 mg (1.23 mmol) of the product of Step A in 6 mL of methanol was added 540 μL (2.71 mmol) of 5N sodium hydroxide. The reaction mixture was allowed to stir overnight after which TLC analysis (90:10:1 chloroform/methanol/acetic acid) indicated the saponification had proceeded to completion. The reaction mixture was acidified to pH=2 using 6N HCl, poured into water, and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered and evaporated in vacuo to give the crude product. Purification of the crude product by silica-gel flash chromatography using (92:7:1 chloroform/methanol/acetic acid) afforded 384 mg (70%) of the title compound as an amorphous solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give the crude product
  6. customPurification of the crude product by silica-gel flash chromatography

Sources & evidence

ORD record
ord-7133d350f535422a820905cc32a1e0d1
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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