Hydrochloric Acid → HCID 12017649, compound

HRID 1006526Notes

Reaction equation

HRID 1006526 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:12]=2[C:13]([NH:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=2)=[O:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O>C1COCC1.CO.[OH-].[Na+]>[C:1]1([S:7]([NH:10][C:11]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:12]=2[C:13]([NH:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[O:14])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 12017648HCID 12017648, compound

Product 1

HCID 12017649HCID 12017649, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(2-phenylsulfonylamino-5-chlorobenzoyl-amino)benzoate (122 mg; prepared in Example 1.) in THF-MeOH (4 ml+2 ml), 2N NaOH aqueous solution (0.5 ml) was added at room temperature. The mixture was stirred overnight. To the reaction mixture, 2N HCl (0.6 ml) and water were added. The mixture was extracted with ethyl acetate. The organic layer was washed, dried over and concentrated under reduced pressure. The residue was purified by recrystallization from the mixture of AcOEt-hexane to give the title compound (80 mg) having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by recrystallization from the mixture of AcOEt-hexane

Sources & evidence

ORD record
ord-627a9e09add04e06a29e3c6607dbac18
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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