Lithium hydroxide, monohydrate → HCID 10136668, compound
Reaction equation
[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[N:4]([CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([O:30][CH2:31][CH3:32])[C:25]([O:27]CC)=[O:26])=[CH:19][CH:18]=2)[CH2:3]1.O.[OH-].[Li+]>>[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[N:4]([CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH:24]([O:30][CH2:31][CH3:32])[C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH2:3]1Participants
3
Procedure
Ethyl 3-[4-{3-(2-methyl-7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)propylamino}phenyl]-2-ethoxypropanoate (320 mg, 1 eq, 0.72 mmol) obtained in example 52, was hydrolyzed using lithium hydroxide monohydrate (46 mg, 1.5 eq, 1.08 mmol), in methanol-THF-water at RT till all the starting material is consumed (4 to 5 h). The reaction mixture was diluted with water, acidified (pH ˜4-5) with dil. HCl and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated on rotary evaporator. The residue was chromatoghaphed using methanol and chloroform to afford the title compound (190 mg, yield 64%) as viscous liquid.
Workup
- custom