Lithium Hydroxide → (S)-4-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)-3-fluorobenzoic acid
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([F:32])[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:18][CH2:17][C@H:16]([O:19][C:20]4[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][C:21]=4[F:30])[C:15]3=[O:31])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([F:32])[C:5]([N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[CH2:18][CH2:17][C@H:16]([O:19][C:20]4[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=4[F:30])[C:15]3=[O:31])[CH2:12][CH2:13]2)=[N:6][CH:7]=1Komponenten
4
Versuchsvorschrift
To a solution of (S)-methyl 4-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)-3-fluorobenzoate (1.5 g, 3.2 mmol) in THF (30 mL) was added 3 N lithium hydroxide (4.3 mL, 13 mmol) and the reaction was stirred overnight at ambient temperature. Additional 3 N LiOH (4.3 mL, 13 mmol) was added, and the reaction was stirred for an additional 3 hours. The THF was removed with a stream of nitrogen. The aqueous layer was acidified by addition of HCl (1 N) and the solid that formed was filtered and washed with water. The solid was dried under vacuum to yield (S)-4-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)-3-fluorobenzoic acid (1.3 g, 2.9 mmol, 89% yield).