Hydrochloric Acid → HCID 136166851, compound

HRID 1617582Notes

Reaction equation

HRID 1617582 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18][C:19](=[N:27][OH:28])[C:20]3[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].Cl>COCCOC.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH2:18]/[C:19](=[N:27]\[OH:28])/[C:20]3[CH:25]=[CH:24][N:23]=[C:22]([CH3:26])[CH:21]=3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136360007HCID 136360007, compound

Product 1

HCID 136166851HCID 136166851, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-fluoro-4′-[3-[hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (example 112; 151 mg) in DME (2.5 mL) was added HCl in dioxane (4M, 0.8 mL) at rt. The reaction mixture was stirred at 50° C. for 4 hours, was concentrated and dissolved in ethyl acetate (5 mL) and a saturated aqueous solution of NaHCO3 (0.1 mL). A saturated aqueous solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give 3-fluoro-4′-[3-[(E)-hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid as a yellow solid, MS (ESI+): m/z=469.3 ([M+H]+).

Workup

  1. concentrationwas concentrated
  2. dissolutiondissolved in ethyl acetate (5 mL)
  3. additionA saturated aqueous solution of NH4Cl was added
  4. customthe phases were separated
  5. extractionthe inorganic one was extracted with EtOAc (2×)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf3a109f5cd04bfd9e62349645c7a848
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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