Sodium Hydroxide → 4-[4-(4-Methyl-benzoylamino)-phenyl]-4-oxo-butyric acid

HRID 1264092Notes

Reaction equation

HRID 1264092 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[O:7])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 120168344-[4-(4-Methyl-benzoylamino)-phenyl]-4-oxo-butyric acid, methyl ester

Product 1

HCID 99227354-[4-(4-Methyl-benzoylamino)-phenyl]-4-oxo-butyric acidYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, partial solution of 4-[4-(4-methyl-benzoylamino)-phenyl]-4-oxo-butyric acid, methyl ester (0.5748 g, 0.00177 mol) in THF (11 mL) was added 1.0 M NaOH (3.7 mL, 0.0037 mol), and the mixture was stirred overnight. The resulting suspension was filtered, and the filtercake was washed with THF. The solids were partitioned between EtOAc-THF and 0.2 M HCl, and left for 8 days. The solids were filtered, washed with water, and dried in vacuo to give 0.2133 g of 4-[4-(4-methyl-benzoylamino)-phenyl]-4-oxo-butyric acid as an off-white solid; mp 257-258° C.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe filtercake was washed with THF
  3. customThe solids were partitioned between EtOAc-THF and 0.2 M HCl
  4. waitleft for 8 days
  5. filtrationThe solids were filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-72ba7fb5b14345aca33f5a201b08195d
Source dataset
uspto-grants-2003_04
Patent number
US06541521B1

Reaction notes

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