Potassium Hydroxide → N-[4-(4-Hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-malonamic acid

HRID 584007Notes

Reaction equation

HRID 584007 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][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]([CH:23]([CH3:25])[CH3:24])[CH:17]=2)=[C:10]([CH3:26])[CH:9]=1)=[O:6].[OH-].[K+]>CO.O>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:11]2[C:10]([CH3:26])=[CH:9][C:8]([NH:7][C:5](=[O:6])[CH2:4][C:3]([OH:27])=[O:2])=[CH:13][C:12]=2[CH3:14])=[CH:17][C:18]=1[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12114180N-[4-(4-Hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-malonamic acid methyl ester

Product 1

HCID 10269704N-[4-(4-Hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-malonamic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of N-[4-(4-hydroxy-3-isopropyl-phenoxy)-3,5-dimethyl-phenyl]-malonamic acid methyl ester (29 mg, 0.08 mmol) in a mixture of MeOH (1 mL) and H2O (1 mL) was added 3 N KOH (0.9 mmol, 0.3 mL). After stirring at RT for 4 h, H2O (10 mL) was added. The solution was washed with EtOAc (2×10 mL) and acidified with 1 N HCl. The aqueous solution was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine, dried and concentrated to give the title compound of Step E and Example 1 (20 mg) as a white solid. MS (APCl−) Calc.: 357.1. Found: 356.1 (M−1).

Workup

  1. washThe solution was washed with EtOAc (2×10 mL)
  2. extractionThe aqueous solution was extracted with EtOAc (3×10 mL)
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a9ef416b15045bfb021c822c50497a9
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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