Sodium Hydroxide → 4-({[4-Chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}methyl)benzoic acid

HRID 520941Notes

Reaction equation

HRID 520941 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)=[C:4]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:25]=2)(=[O:23])=[O:22])[CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)=[C:4]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:32])([F:33])[F:34])[CH:25]=2)(=[O:23])=[O:22])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71738701Methyl 4-(((4-chloro-2-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)phenyl)thio)methyl)benzoate

Product 1

HCID 717386304-({[4-Chloro-2-({[4-chloro-3-(trifluoromethyl)phenyl]sulfonyl}amino)phenyl]sulfanyl}methyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(((4-chloro-2-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)phenyl)thio)methyl)benzoate (635 mg, 1.155 mmol), NaOH (5M, 2 ml) in MeOH (10 ml) was stirred at room temperature overnight. The solvent was removed and the residue was diluted with water, acidified with 10% HCl. The mixture was extracted with EtOAc (2×20 ml). The combined organic layer was washed with brine and concentrated under vacuum. The desire product was purified by MPLC (50% to 100% EtOAc/Hexane).

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with water
  3. extractionThe mixture was extracted with EtOAc (2×20 ml)
  4. washThe combined organic layer was washed with brine
  5. concentrationconcentrated under vacuum
  6. customThe desire product was purified by MPLC (50% to 100% EtOAc/Hexane)

Sources & evidence

ORD record
ord-0eda60131c134292aaa920b3f9db4ab5
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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