Hydrochloric Acid → 3-[1-(2,4-Dimethoxybenzyl)-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid

HRID 2261392Notes

Reaction equation

O[Li].O.C[O:5][C:6](=[O:27])[CH2:7][CH2:8][C:9]1[C:10](=[O:26])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH3:25])[CH2:12][CH2:13][CH:14]=1.Cl>C1COCC1>[CH3:25][O:24][C:17]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=1[CH2:15][N:11]1[CH2:12][CH2:13][CH:14]=[C:9]([CH2:8][CH2:7][C:6]([OH:27])=[O:5])[C:10]1=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

11 mg of LiOH.H2O solution (0.26 mmol) was added to 0.75 ml of THF solution containing 58 mg of 3-[1-(2,4-dimethoxy benzyl)-2-oxo-1,2,5,6-tetrahydro pyridine-3-yl]-propionic acid methyl ester (d) (0.17 mmol) in a dropwise manner at 0° C. After the reaction mixture was stirred for 2 hrs at 0° C. and for 1 hr at room temperature, 5% HCl was added to the mixture to pH 2. Then the mixture was extracted three times with 10 ml of ethyl acetate, the organic layer was washed with saturated NaCl solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with methanol/chloroform (1:10) solvent mixture as an eluant to give 44 mg of the title compound (f1) (yield: 80%).

Workup

extractionThen the mixture was extracted three times with 10 ml of ethyl acetate
washthe organic layer was washed with saturated NaCl solution
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting compound was purified with Silica gel column chromatography with methanol/chloroform (1:10) solvent mixture as an eluant

Sources & evidence

ORD record: ord-fcd0c703113844ce9bca477ba2996bd6
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846963B2

Reaction notes

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