Hydrochloric Acid → HCID 11454476, compound

HRID 2373346Notes

Reaction equation

HRID 2373346 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH2:25][C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[C:16]([C:19]([O:21]CC)=[O:20])[NH:17][N:18]=3)[CH:9]=2)[CH:7]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH2:25][C:26]([F:34])([F:35])[C:27]([F:33])([F:32])[C:28]([F:30])([F:31])[F:29])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[N:15]=[C:16]([C:19]([OH:21])=[O:20])[NH:17][N:18]=3)[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86602751HCID 86602751, compound

Product 1

HCID 11454476HCID 11454476, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.1 g (0.196 mmol) of ethyl 5-[5′-fluoro-2′-(2,2,3,3,4,4,4-heptafluorobutyloxy)biphenyl-3-yl]2H-1,2,4-triazole-3-carboxylate (prepared according to procedures described in Reference Example 3, Step B) in 1.4 mL of methanol was added 0.59 mL (0.59 mmol) of a 1N aqueous solution of NaOH and the reaction mixture was stirred at rt for 23 hr. The pH of the reaction mixture was adjusted to pH=4-5 with 1N HCl solution and the mixture was extracted with EtOAc. The organic fractions were dried (Na2SO4), filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, CH2Cl2:acetone 9:1, then CH3OH: CH2Cl2 1 to 10% linear gradient) to give the title compound.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic fractions were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, CH2Cl2:acetone 9:1

Sources & evidence

ORD record
ord-dca8cd2176d04e2a86aa1ba9fc0405c4
Source dataset
uspto-grants-2008_12
Patent number
US07459475B2

Reaction notes

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