Lithium Hydroxide → 6-((2R,4S)-4-fluoro-2-(5-fluoro-2-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1054464Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([N:15]3[CH2:19][C@@H:18]([F:20])[CH2:17][C@@H:16]3[C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=3[O:28][C@H:29]3[CH2:33][CH2:32][O:31][CH2:30]3)[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)=[O:5])C.[Li+].[OH-]>C(O)C>[F:20][C@@H:18]1[CH2:19][N:15]([C:12]2[CH:13]=[CH:14][C:9]3[N:10]([C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=3)[CH:11]=2)[C@@H:16]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[O:28][C@H:29]2[CH2:33][CH2:32][O:31][CH2:30]2)[CH2:17]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a stirred solution of Ethyl-6-((2R,4S)-4-fluoro-2-(5-fluoro-2-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylate (1.3 g, 28.43 mmol) in ethanol was added 1M LiOH (2.6 ml) solution and stirred for 5 h at 85° C. Solvent was removed under reduced pressure and residue was dissolved in water, extracted unwanted impurities with Diethyl ether and water was acidified with 2N HCl and solid was collected by filtration. Solid was dried under high vacuum to afford 6-((2R,4S)-4-fluoro-2-(5-fluoro-2-(((S)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (1.0 g, yield: 82%). MS (ESI): 430 (M+H).

Workup

customSolvent was removed under reduced pressure and residue
dissolutionwas dissolved in water
extractionextracted unwanted impurities with Diethyl ether and water
filtrationwas collected by filtration
customSolid was dried under high vacuum

Sources & evidence

ORD record: ord-a2a18c94ca004d548498e7341f453aac
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394305B2

Reaction notes

Loading…