Reaction #2329063

ord-793147be80864a7c877625f73227efd7

Reaction equation

COC(=O)Cc1cnc(NS(=O)(=O)c2cccc(Cl)c2C)s1
methyl (2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetate
[K+].[OH-]
KOH
Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1
product
Yield 104.9%
Cc1c(Cl)cccc1S(=O)(=O)Nc1ncc(CC(=O)O)s1
(2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1.3-thiazol-5-yl)acetic acid
Yield 104.9%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was then removed under reduced pressure
  2. 2
    workup.DISSOLUTIONthe crude product dissolved in water
  3. 3
    Otherprecipitated
  4. 4
    FiltrationFiltration
  5. 5
    Washwashing with water (5 mL)

Procedure

To methyl (2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-5-yl)acetate (Example 2) (0.2 g, 0.55 mmol) dissolved in EtOH (5.5 mL) was added aqueous KOH (0.6 mL, 5.5 M). The reaction mixture was stirred at room temperature for 1 h. The solvent was then removed under reduced pressure and the crude product dissolved in water. The aqueous phase was acidified using conc. HCl so that the product precipitated. Filtration and washing with water (5 mL) afforded 0.2 g, 97% product. The product was used without any further purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07671051B2uspto-grants-2010_03