Sodium Hydroxide → 4-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoic acid

HRID 541452Notes

Reaction equation

[CH:1]1([C:5]2[C:14]([C:15]3[CH:19]=[C:18]([CH2:20][CH3:21])[NH:17][N:16]=3)=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:5]2[C:14]([C:15]3[CH:19]=[C:18]([CH2:20][CH3:21])[NH:17][N:16]=3)=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:22])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 4-cyclobutyl-5-(5-ethyl-1H-pyrazol-3-yl)-2-methylbenzoate (compound 445.2, 188 mg, 0.630 mmol, 1.00 equiv) in methanol (6 mL) was added aqueous sodium hydroxide (76.0 mg, 1.90 mmol, 3.00 equiv in 3 mL water). The resulting solution was stirred for 2 h at 70° C. in an oil bath. After cooling to ambient temperature, the mixtue was concentrated under reduced pressure. The residue was diluted with 20 mL of H2O. The pH of the mixture was adjusted to −4 with aqueous HCl (2 M). The mixture was then extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with 3×20 mL of brine, dried (Na2SO4), and concentrated under reduced pressure. This resulted in 0.180 g (crude) of the title compound as a yellow oil.

Workup

temperatureAfter cooling to ambient temperature
concentrationthe mixtue was concentrated under reduced pressure
additionThe residue was diluted with 20 mL of H2O
extractionThe mixture was then extracted with 3×20 mL of ethyl acetate
washThe combined organic layers were washed with 3×20 mL of brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ce8a0638316147a6988935ccf160b2e4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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