Water → 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionic acid

HRID 2047997Notes

Reaction equation

HRID 2047997 reaction equation
O.[OH-].[Li+].O.[F:5][C:6]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH3:19])=[C:12]2[C:7]=1[C:8](=[O:37])[C:9]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[CH:10][N:11]2[CH2:20][CH2:21][S:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26]>C(#N)C>[F:5][C:6]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH3:19])=[C:12]2[C:7]=1[C:8](=[O:37])[C:9]([C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)=[CH:10][N:11]2[CH2:20][CH2:21][S:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 58492496methyl 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionate

Product 1

HCID 584925053-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Lithium hydroxide mono-hydrate (31 mg, 0.74 mmol) and water (5 ml) were added to an acetonitrile solution (10 ml) of methyl 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionate (175 mg, 0.37 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with ethyl acetate, and then 2N hydrochloric acid was added to the water layer to make the mixture acidic. The generated insoluble matter was separated, washed with water and then dried, giving a white powder of 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethylsulfanyl}propionic acid (140 mg, yield: 82%).

Workup

  1. washThe reaction mixture was washed with ethyl acetate
  2. addition2N hydrochloric acid was added to the water layer
  3. customThe generated insoluble matter was separated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-567bcbc09c6f4ce2bc33d13df6861e0d
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

Loading…