Hydrochloric Acid → HCID 89906548, compound

HRID 526704Notes

Reaction equation

HRID 526704 reaction equation
C([O:3][C:4](=[O:34])[C:5]([O:8][CH2:9][C:10]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[N:12]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=2[Cl:33])[N:11]=1)([CH3:7])[CH3:6])C.[Li+].[OH-].Cl>C1COCC1.O>[Cl:33][C:27]1[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:26]=1[N:12]1[C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:21]=2)=[C:14]([CH3:15])[C:10]([CH2:9][O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:34])=[O:3])=[N:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89907577HCID 89907577, compound

Product 1

HCID 89906548HCID 89906548, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g of 2-[1-(2,4-Dichloro-phenyl)-4-methyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazol-3-ylmethoxy]-2-methyl-propionic acid ethyl ester in 6 ml THF was added a solution of 232 mg of LiOH in 1 ml water at room temperature. After 16 h the mixture was brought to pH 2 by addition of 1 M hydrochloric acid. The reaction mixture was concentrated under reduced pressure and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The residue was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were evaporated and lyophilized to yield a yellow solid. Yield: 634 mg.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe residue was purified by preparative HPLC (
  6. washC18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA)
  7. additionThe fractions containing the product
  8. customwere evaporated
  9. customto yield a yellow solid

Sources & evidence

ORD record
ord-66562a85996d4f08b5e82c4b33451374
Source dataset
uspto-grants-2016_05
Patent number
US09346762B2

Reaction notes

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