Hydrochloric Acid → HCID 15380230, compound

HRID 375663Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ethyl[4-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-1H-pyrazol-1-yl]acetate from Step 1 (1.05 g, 2.6 mmol) in THF (20 mL) was added 3.0 mL of aqueous in lithium hydroxide at 25° C. under nitrogen and the mixture stirred at 25° C. for 24 hours. The mixture was acidified with 2N HCl, extracted with two portions ethyl acetate and the organic layer separated, washed with brine, dried over MgSO4 and concentrated in vacuo. Chromatographic purification on silica gel using 20% ethanol/79% chloroform/1% acetic acid as the eluant gave [4-(4-Fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-1H-pyrazol-1-yl]acetic acid as a white solid (0.58 g, 60%). Elemental analysis for C18H15N2FSO4 +0.8 CH3CO2H Calc'd: C, 55.73, H, 4.34, N, 6.63, S, 7.59. Found: C, 55.72, H, 4.35, N, 6.74, S, 7.72.

Workup

extractionextracted with two portions ethyl acetate
customthe organic layer separated
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customChromatographic purification on silica gel using 20% ethanol/79% chloroform/1% acetic acid as the eluant

Sources & evidence

ORD record: ord-21725cf089594ec8bd11e2b666a862a4
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486534

Reaction notes

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