Lithium Hydroxide → 3-Cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid

HRID 1935255Notes

Reaction equation

C[O:2][C:3](=[O:23])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Li+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][CH:16]=2)[C:3]([OH:23])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid methyl ester (450 mg, 1.45 mmol) in tetrahydrofuran (5 mL) was treated with a 0.8M aqueous lithium hydroxide solution (2.18 mL, 1.74 mmol). The resulting reaction mixture was stirred at 25° C. for 3 d. The reaction mixture was then partitioned between water (50 mL) and ethyl acetate (50 mL), and the layers were separated. The aqueous layer was further extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was purified by precipitation from methylene chloride/ethyl acetate to afford 3-cyclopentyl-2-(4-pyridin-3-yl-phenyl)-propionic acid (271 mg, 63%) as a white solid: mp 136-138° C.; EI-HRMS m/e calcd for C19H21NO2 (M+) 295.1572, found 295.1572.

Workup

customThe resulting reaction mixture
customThe reaction mixture was then partitioned between water (50 mL) and ethyl acetate (50 mL)
customthe layers were separated
extractionThe aqueous layer was further extracted with ethyl acetate (2×50 mL)
dry with materialThe combined organic extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting solid was purified by precipitation from methylene chloride/ethyl acetate

Sources & evidence

ORD record: ord-3ecb16cf64f24762801766d4415f0dfc
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384220B2

Reaction notes

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