Hydrochloric Acid → HCID 57742491, compound

HRID 2266460Notes

Reaction equation

HRID 2266460 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:26][CH:27]([F:29])[F:28])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:10]([CH3:17])=[N:11]2.C[O:32][C:33](=[O:60])[CH2:34][O:35][C:36]1[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]2[C:37]=1[C:38]([CH3:59])=[C:39]([CH2:51][C:52]1[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=1)[C:40]([O:47][CH:48]([F:50])[F:49])=[N:41]2.[OH-].[Li+].Cl>O.CO>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:30])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:17])[C:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)=[C:8]2[O:26][CH:27]([F:29])[F:28].[Cl:46][C:43]1[CH:44]=[CH:45][C:36]([O:35][CH2:34][C:33]([OH:60])=[O:32])=[C:37]2[C:42]=1[N:41]=[C:40]([O:47][CH:48]([F:49])[F:50])[C:39]([CH2:51][C:52]1[CH:53]=[CH:54][C:55]([F:58])=[CH:56][CH:57]=1)=[C:38]2[CH3:59]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68779899HCID 68779899, compoundHCID 68780268HCID 68780268, compound

Product 2

HCID 57742491HCID 57742491, compoundHCID 57742506HCID 57742506, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of [8-chloro-4-difluoromethoxy-3-(4-fluorobenzyl)-2-methylquinolin-5-yloxy]acetic acid methyl ester and [8-chloro-2-difluoromethoxy-3-(4-fluorobenzyl)-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.26 g), methanol (5.0 mL), water (3.0 mL) and lithium hydroxide solution (0.13 g mL) was stirred at room temperature for 1 hour. The solution was acidified by the addition of hydrochloric acid, extracted with ethyl acetate and the combined extracts dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile—(in water to afford [8-chloro-4-difluoromethoxy-3-(4-fluorobenzyl)-2-methylquinolin-5-yloxy]acetic acid as a white solid, 0.032 g and [8-chloro-2-difluoromethoxy-3-(4-fluorobenzyl)-4-methylquinolin-5-yloxy]acetic acid as a white solid, 0.029 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined extracts dried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by preparative reverse-phase
  5. customover 30 minutes

Sources & evidence

ORD record
ord-c0c89bcb49574f869f52828340c3dab5
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

Loading…