Hydrochloric Acid → HCID 11278150, compound

HRID 2261370Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

10.8 mg of LiOH.H2O solution (0.25 mmol) was added to 0.86 ml of THF solution containing 55 mg of 3-[1-(2,4-dimethoxy benzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-propionic acid methyl ester (0.17 mmol) in a dropwise manner at 0° C. The reaction mixture was stirred for 2 hrs at 0° C. and 5% HCl was added to pH 1. Then the mixture was extracted three times with 10 ml of ethyl acetate, the organic layer was washed with 15 ml of saturated NaCl solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:9) as an eluant to give 41 mg of 3-[1-(2,4-dimethoxy-benzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-propionic acid (16f) (yield: 80%).

Workup

extractionThen the mixture was extracted three times with 10 ml of ethyl acetate
washthe organic layer was washed with 15 ml of saturated NaCl solution
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting compound was purified with Silica gel column chromatography with a solvent mixture
additionmixed with methanol and chloroform (1:9) as an eluant

Sources & evidence

ORD record: ord-d4518da4d34541f98cacb221f32703ff
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846963B2

Reaction notes

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