Lithium Hydroxide → HCID 10111454, compound

HRID 1297596Notes

Reaction equation

C([O:3][C:4](=[O:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([C:16]2[C:17]([O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])=[C:8]([F:30])[CH:7]=1)C.[OH-].[Li+]>O1CCCC1.O>[F:30][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([OH:31])=[O:3])[CH:11]=[CH:10][C:9]=1[CH2:12][NH:13][C:14]([C:16]1[C:17]([O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:15]

Participants

Conditions

Temperature: 55 °C

Procedure

[3-Fluoro-4-({[2-(4-fluoro-phenoxy)-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-acetic acid ethyl ester (1.45 g) was combined with lithium hydroxide (0.59 g) in a 30 mL solution of tetrahydrofuran:water (2:1). The reaction mixture was heated to 55° C. in an oil bath for 1 h. The reaction mixture was allowed to cool to ambient temperature, and the organic solvent was removed in vacuo. The remaining portion of the reaction mixture was brought to pH=3 with 3N hydrochloric acid. The mixture was extracted with ethyl acetate (5×40 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated to dryness in vacuo. The crude product was purified by recrystallization (ethyl acetate) to yield the pure product (0.700 g).

Workup

temperatureto cool to ambient temperature
customthe organic solvent was removed in vacuo
extractionThe mixture was extracted with ethyl acetate (5×40 mL)
dry with materialThe combined organics were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness in vacuo
customThe crude product was purified by recrystallization (ethyl acetate)

Sources & evidence

ORD record: ord-2767408854c14c4aa4bbcc101f0ab50e
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250518B2

Reaction notes

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