Lithium Hydroxide → 3-(1-(4-chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionic Acid

HRID 2059892Notes

Reaction equation

C([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[S:13]([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([Cl:23])=[CH:18][C:17]=1[CH3:24])(=[O:15])=[O:14])C.[OH-].[Li+]>CO.O>[Cl:23][C:19]1[C:20]([CH3:22])=[CH:21][C:16]([S:13]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]2[CH2:6][CH2:5][C:4]([OH:25])=[O:3])(=[O:14])=[O:15])=[C:17]([CH3:24])[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methanol/H2O (3:1, 90 ml) was added to 3-(1-(4-chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionic acid ethyl ester (3.48 g, 9 mmol) at 25° C., the mixture was cooled to 0° C., lithium hydroxide (0.75 g, 18 mmol) was added, and the mixture was stirred for 16 h at 25° C. The solvent was removed under vacuum, the residue taken up in water and washed with dichloromethane. The aqueous phase was carefully acidified with hydrogen chloride solution (1 mol/l) and extracted with ethyl acetate. This organic phase was washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated to small volume under vacuum. Yield: 89%

Workup

customThe solvent was removed under vacuum
washwashed with dichloromethane
extractionextracted with ethyl acetate
washThis organic phase was washed with water and saturated sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record: ord-3ac86b6d22ac4b009d855903a4859560
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278319B2

Reaction notes

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