Water → 2,2-dimethyl-3-phenyl-3-(3-phenyl-1H-indazol-6-yl)propanoic acid

HRID 563394Notes

Reaction equation

[CH3:1][C:2]([CH3:29])([CH:7]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:16]=[C:15]2[C:11]([C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:13][NH:14]2)=[CH:10][CH:9]=1)[C:3]([O:5]C)=[O:4].O.[OH-].[Li+].O>O1CCOCC1>[CH3:1][C:2]([CH3:29])([CH:7]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:16]=[C:15]2[C:11]([C:12]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[N:13][NH:14]2)=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of methyl 2,2-dimethyl-3-phenyl-3-(3-phenyl-1H-indazol-6-yl)propanoate (45 mg, 0.12 mmol), lithium hydroxide monohydrate (50 mg, 1.2 mmol), water (2 mL), and dioxane (4 mL) was stirred at 110° C. overnight. The mixture was cooled to rt and partitioned between water (5 mL) and diethyl ether (10 mL). The ether layer was extracted with water (10 mL). The combined aqueous solutions were acidified with 6N hydrochloric acid, extracted with ethyl acetate (15 mL), washed with brine (10 mL), dried (Na2SO4) and concentrated to give 2,2-dimethyl-3-phenyl-3-(3-phenyl-1H-indazol-6-yl)propanoic acid (46 mg, 0.12 mmol, 100% yield) as a glassy solid.

Workup

temperatureThe mixture was cooled to rt
custompartitioned between water (5 mL) and diethyl ether (10 mL)
extractionThe ether layer was extracted with water (10 mL)
extractionextracted with ethyl acetate (15 mL)
washwashed with brine (10 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-dead6fb7de984270be42ef91c23426bf
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067447B2

Reaction notes

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