Citric Acid → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-4-phenylbutanoic acid

HRID 563409Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:18]([CH3:24])([CH3:23])[C:19]([O:21]C)=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.CCOCC.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:18]([CH3:23])([CH3:24])[C:19]([OH:21])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-4-phenylbutanoate (210 mg, 0.50 mmol), lithium hydroxide monohydrate (80 mg, 1.9 mmol), water (3 mL), and dioxane (6 mL) was stirred at 90° C. for 24 hr under nitrogen. The reaction mixture was cooled to rt before diethyl ether (20 mL) was added. The ether layer was reextracted with water (2×3 mL). The combined aqueous solutions were acidified with aqueous 10% citric acid solution and extracted with ethyl acetate (3×6 mL). The combined ethyl acetate extracts were dried (Na2SO4) and concentrated to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-4-phenylbutanoic acid (200 mg, 0.50 mmol, 100% yield) as a solid.

Workup

additionwas added
extractionextracted with ethyl acetate (3×6 mL)
dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-8bd728d6cc684c02ae446c80a119b72c
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067447B2

Reaction notes

Loading…