Hydrochloric Acid → N-[3,5-dibromo-4-[3-formyl-4-hydroxy-5-isopropylphenoxy]-2-methylphenyl]malonamic acid

HRID 1392556Notes

Reaction equation

HRID 1392556 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Br:15])[C:12]([O:16][C:17]2[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:26])=[C:19]([CH:27]=[O:28])[CH:18]=2)=[C:11]([Br:29])[C:10]=1[CH3:30])=[O:7])C.[Li+].[OH-].Cl>C1COCC1>[Br:29][C:11]1[C:10]([CH3:30])=[C:9]([NH:8][C:6](=[O:7])[CH2:5][C:4]([OH:31])=[O:3])[CH:14]=[C:13]([Br:15])[C:12]=1[O:16][C:17]1[CH:22]=[C:21]([CH:23]([CH3:24])[CH3:25])[C:20]([OH:26])=[C:19]([CH:27]=[O:28])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59678444N-[3,5-dibromo-4-[3-formyl-4-hydroxy-5-isopropylphenoxy]-2-methyl-phenyl]malonamic acid ethyl ester

Product 1

HCID 10052681N-[3,5-dibromo-4-[3-formyl-4-hydroxy-5-isopropylphenoxy]-2-methylphenyl]malonamic acidYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound N-[3,5-dibromo-4-[3-formyl-4-hydroxy-5-isopropylphenoxy]-2-methyl-phenyl]malonamic acid ethyl ester of Part 8F (15 mg, 0.027 mmol) and THF (0.5 mL) was added LiOH (0.25 mL, 1N). After 1 hour of stirring the pH of reaction was adjusted to 1 with 1N HCl and the organic phase removed in vacuo. The residue was extracted with EtOAc (3×3 mL) and the combined organic phases were dried over Na2SO4 before concentration. The residue was purified on column (silica gel, gradient elution: CHCl3/MeOH/AcOH from 1:0:0 to 90:10:1) to yield 6 mg (42%) of N-[3,5-dibromo-4-[3-formyl-4-hydroxy-5-isopropylphenoxy]-2-methylphenyl]malonamic acid as a white solid.

Workup

  1. customthe pH of reaction
  2. customthe organic phase removed in vacuo
  3. extractionThe residue was extracted with EtOAc (3×3 mL)
  4. dry with materialthe combined organic phases were dried over Na2SO4 before concentration
  5. customThe residue was purified on column (silica gel, gradient elution: CHCl3/MeOH/AcOH from 1:0:0 to 90:10:1)

Sources & evidence

ORD record
ord-82a84b23bf4648869b1f0513b6cd7dc6
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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