Lithium hydroxide, monohydrate → (s)-2-[4-(2-Fluoro-3-pyrrolidin-1-yl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid lithium salt

HRID 19158Notes

Reaction equation

C([O:3][C:4](=[O:29])[C@@H:5]([N:10]1[CH2:14][C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:17]=2[F:27])=[CH:12][C:11]1=[O:28])[CH2:6][CH:7]([CH3:9])[CH3:8])C.O.[OH-].[Li+:32]>O1CCCC1>[Li+:32].[F:27][C:17]1[C:18]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C:13]1[CH2:14][N:10]([C@@H:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([O-:29])=[O:3])[C:11](=[O:28])[CH:12]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution containing (S)-2-[4-(2-fluoro-3-pyrrolidin-1-yl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester (0.120 g, 0.29 mmol) in tetrahydrofuran (4 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 1.2 mL, 0.6 mmol). The mixture was stirred at 25° C. for 2 h, and the solvents evaporated. The residue was rinsed with diethyl ether which afforded (S)-2-[4-(2-fluoro-3-pyrrolidin-1-yl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid lithium salt (0.140 g, 100%) as a yellow solid.

Workup

customthe solvents evaporated
washThe residue was rinsed with diethyl ether which

Sources & evidence

ORD record: ord-1975987fe34a4f76bffb36371302f57d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

Loading…