Reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[N:6][C:5]=1[NH:11][CH2:12][C:13]([N:15]1[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH2:17][C@H:16]1[CH3:30])=[O:14].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:10][C:8]1[CH:7]=[N:6][C:5]([NH:11][CH2:12][C:13]([N:15]2[CH2:20][C@H:19]([CH3:21])[N:18]([CH2:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[CH2:17][C@H:16]2[CH3:30])=[O:14])=[C:4]([CH:9]=1)[C:3]([OH:31])=[O:2]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-nicotinic acid methyl ester (0.16 g, 0.36 mmol) in tetrahydrofuran (3 mL), methanol (3 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.075 g, 1.78 mmol). The reaction was stirred at ambient temperature overnight, concentrated in vacuo, diluted with dichloromethane and passed through a glass frit. The filtrate was treated with diethyl ether saturated with hydrogen chloride gas, and the white precipitate thus formed was collected by filtration to give the title compound as its hydrochloride salt (0.13 g).
Workup
- concentrationconcentrated in vacuo
- additiondiluted with dichloromethane
- additionThe filtrate was treated with diethyl ether saturated with hydrogen chloride gas
- customthe white precipitate thus formed
- filtrationwas collected by filtration
Sources & evidence
- ORD record
- ord-223a3321ac374d05890573b86de32568
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098212B2
Linked notes
Loading…