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

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Reaction Steps

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.

Provenance & Evidence