Lithium Hydroxide → [4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid

HRID 377691Notes

Reaction equation

C([O:3][C:4](=[O:32])[CH2:5][N:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[C:9]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:8]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[N:7]1)C.[OH-].[Li+]>O1CCCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:9]2[C:8]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:24][CH:23]=3)=[N:7][N:6]([CH2:5][C:4]([OH:32])=[O:3])[C:10]=2[C:11]([F:14])([F:12])[F:13])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ethyl[4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetate (Example 8) (0.48 g, 1.0 mmol) in tetrahydrofuran (THF) (10 mL) was added 1.5 mL of 1N aqueous lithium hydroxide at 25° C. under nitrogen and the mixture stirred for 24 hours at 25° C. The reaction mixture was extracted with two portions diethyl ether and the aqueous layer was acidified with dilute aqueous HCl. This was extracted with two portions ethyl acetate which was washed with brine, dried over MgSO4 and concentrated in vacuo. Recrystallization from chloroform/acetone gave [4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid as a white crystalline solid (0.41 g, 93%). Elemental analysis for C19H14N2F4SO4Calc'd: C, 51.58, H, 3.19, N, 6.33. Found: C, 51.18, H, 3.23, N, 6.19.

Workup

extractionThe reaction mixture was extracted with two portions diethyl ether
extractionThis was extracted with two portions ethyl acetate which
washwas washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customRecrystallization from chloroform/acetone

Sources & evidence

ORD record: ord-753b60537c7d4de8a0c6a40c9ac10b65
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028072

Reaction notes

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