Lithium Hydroxide → HCID 10323518, compound

HRID 2218132Notes

Reaction equation

C[O:2][C:3](=[O:38])[CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[O:28])=[CH:22][CH:21]=3)[C:15]2=[O:37])=[CH:9][CH:8]=1)[CH3:6].[OH-].[Li+]>O1CCCC1>[O:37]=[C:15]1[C:16]([C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])=[O:28])=[CH:22][CH:21]=2)=[CH:17][CH:18]=[CH:19][N:14]1[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH:5]([CH3:6])[CH2:4][C:3]([OH:38])=[O:2])=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 65 °C

Procedure

(±)-3-(4-{2-Oxo-3-[4-(3-o-tolyl-ureido)phenyl]-2H-pyridin-1-ylmethyl}phenyl)-butyric acid methyl ester (0.21 g, 0.41 mmol) was dissolved in tetrahydrofuran (3 mL) and aqueous lithium hydroxide (0.5 M, 3 mL) added with stirring. The mixture was heated at 65° C. for 2 hours and then allowed to cool and concentrated in vacuo. The mixture was acidified with hydrochloric acid (2M), extracted with ethyl acetate (2×25 mL) and the combined organic layers washed with brine and dried over anhydrous magnesium sulfate. After filtration and evaporation to dryness the title compound was obtained as a white solid.

Workup

temperatureto cool
concentrationconcentrated in vacuo
extractionextracted with ethyl acetate (2×25 mL)
washthe combined organic layers washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtration and evaporation to dryness the title compound
customwas obtained as a white solid

Sources & evidence

ORD record: ord-66e56039b7bd48d9868c8e818d64222d
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410984B2

Reaction notes

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