Methanol → 4-(6-(4-Hydroxypiperidin-1-yl)-3-methylpicolinamido)-3,5-dimethylbenzoic acid

HRID 1427072Notes

Reaction equation

[OH-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([C:16]([NH:18][C:19]3[C:29]([CH3:30])=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][C:20]=3[CH3:31])=[O:17])[C:13]([CH3:32])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.CO>C1COCC1>[OH:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([C:16]([NH:18][C:19]3[C:20]([CH3:31])=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][C:29]=3[CH3:30])=[O:17])[C:13]([CH3:32])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of aqueous 1N NaOH (1.08 ml) is added to a stirred solution of ethyl 4-[[6-(4-hydroxy-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (223 mg, 0.541 mmol) in THF:MeOH (4 ml:2 ml). After heating at 40° C. for 12 hours, the organic solvent is removed under reduced pressure and the semi-solid is dissolved in water and acidified to pH 3 with aqueous 1N HCl. The resulting precipitate is filtered, washed with water, and dried at 40° C. in a vacuum oven for 12 hours to give the title compound as a white solid (160 mg, 77%). Mass spectrum (m/z): 384.2 (M+1).

Workup

customthe organic solvent is removed under reduced pressure
dissolutionthe semi-solid is dissolved in water
filtrationThe resulting precipitate is filtered
washwashed with water
customdried at 40° C. in a vacuum oven for 12 hours

Sources & evidence

ORD record: ord-b270a22e6b26400e984f11936cc7451b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933098B2

Reaction notes

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