Sodium Hydroxide → N-{4-[3-(4-fluorobenzenesulfonyl)-4-hydroxyphenoxy]-3,5-dimethylphenyl}oxamic acid

HRID 1006724Notes

Reaction equation

HRID 1006724 reaction equation
C([O:3][C:4](=[O:34])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:17]=2)=[C:10]([CH3:33])[CH:9]=1)=[O:6])C.[OH-].[Na+]>CCO>[F:32][C:29]1[CH:28]=[CH:27][C:26]([S:23]([C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=2[OH:22])[O:15][C:11]2[C:12]([CH3:14])=[CH:13][C:8]([NH:7][C:5](=[O:6])[C:4]([OH:34])=[O:3])=[CH:9][C:10]=2[CH3:33])(=[O:25])=[O:24])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10163263N-{4-[3-(4-fluorobenzenesulfonyl)-4-hydroxyphenoxy]-3,5-dimethylphenyl}oxamic acid ethyl ester

Product 1

HCID 9876058N-{4-[3-(4-fluorobenzenesulfonyl)-4-hydroxyphenoxy]-3,5-dimethylphenyl}oxamic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the title E compound, N-{4-[3-(4-fluorobenzenesulfonyl)-4-hydroxy-phenoxy]-3,5-dimethylphenyl}oxamic acid ethyl ester (773 mg, 1.58 mmol) in 15 mL of EtOH is treated with aqueous 1N sodium hydroxide (NaOH; 4.75 mL, 4.75 mmol) at RT. After 1h, the reaction is quenched with aqueous 1N HCl (5.5 mL) and the product is taken up in EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The product is triturated with Et2O and dried in vacuo to afford N-{4-[3-(4-fluorobenzenesulfonyl)-4-hydroxyphenoxy]-3,5-dimethylphenyl}oxamic acid: NMR (DMSO-d6) 2.06 (s, 6H), 6.88 (d, 1H, J=9), 7.03 (dd,1H, J=9,3), 7.13 (d, 1H, J=3), 7.43 (app t, 2H, J=9), 7.61 (s, 2H), 7.94 (dd, 2H, J=9,5),10.5 (s,1H), 10.69 (s, 1H); IR (KBr) 1240, 1481, 1685, 1764; ESI-MS 458 [M-1]−.

Workup

  1. customAfter 1h, the reaction is quenched with aqueous 1N HCl (5.5 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe product is triturated with Et2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-51110404e5b24b259b42e4cc455fab1f
Source dataset
uspto-grants-2004_09
Patent number
US06790978B2

Reaction notes

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