Hydrochloric Acid → HCID 10325679, compound

HRID 1392566Notes

Reaction equation

HRID 1392566 reaction equation
C([O:3][C:4](=[O:33])[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]([CH3:27])[CH:18]=2)=[C:11]([Br:28])[C:10]=1[C:29]([F:32])([F:31])[F:30])=[O:7])C.[Li+].[OH-].Cl>C1COCC1>[Br:28][C:11]1[C:10]([C:29]([F:32])([F:30])[F:31])=[C:9]([NH:8][C:6](=[O:7])[CH2:5][C:4]([OH:33])=[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]([CH3:27])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59678422HCID 59678422, compound

Product 1

HCID 10325679HCID 10325679, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound N-[3,5-dibromo-4-[4-hydroxy-5-isopropyl-3-methylphenoxy]-2-trifluoromethyl-phenyl]malonamic acid ethyl ester of Part 11 G (15 mg, 0.027 mmol) in THF (0.5 mL) was added LiOH (0.25 mL, 1N). After 1 hour stirring the pH of reaction was adjusted to 1 by 1N HCl and the organic phase was removed in vacuo. The resulting mixture was extracted with EtOAc (3×3 mL) and the combined organic phases were dried over Na2SO4 before concentration in vacuo. The residue was purified on column (silica gel, gradient elution, CHCl3/MeOH/AcOH from 1:0:0 to 90:10:1) to give N-[3,5-dibromo-4-[4-hydroxy-5-isopropyl-3-methylphenoxy]-2-trifluoromethylphenyl]malonamic acid as a white solid (6 mg, 42%)

Workup

  1. customthe pH of reaction
  2. customthe organic phase was removed in vacuo
  3. extractionThe resulting mixture was extracted with EtOAc (3×3 mL)
  4. dry with materialthe combined organic phases were dried over Na2SO4 before concentration in vacuo
  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-95ff1223999c472bb543531b414eed5c
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

Loading…