Methanol → HCID 16660248, compound

HRID 2266627Notes

Reaction equation

HRID 2266627 reaction equation
C[O:2][C:3](=[O:33])[C@@H:4]([O:6][C:7]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]2[C:8]=1[C:9]([O:29][CH:30]([F:32])[F:31])=[C:10]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28])[C:11]([CH2:18][CH3:19])=[N:12]2)[CH3:5].C[O:35][C:36](=[O:64])[C@@H:37]([O:39][C:40]1[CH:49]=[CH:48][C:47]([F:50])=[C:46]2[C:41]=1[C:42]([O:62][CH3:63])=[C:43]([CH2:53][C:54]1[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][C:55]=1[Cl:61])[C:44]([CH2:51][CH3:52])=[N:45]2)[CH3:38].CO.[OH-].[Li+]>C(O)(=O)C.O>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[CH2:20][C:10]1[C:11]([CH2:18][CH3:19])=[N:12][C:13]2[C:8]([C:9]=1[O:29][CH:30]([F:31])[F:32])=[C:7]([O:6][C@@H:4]([CH3:5])[C:3]([OH:33])=[O:2])[CH:16]=[CH:15][C:14]=2[F:17].[Cl:61][C:55]1[CH:56]=[C:57]([Cl:60])[CH:58]=[CH:59][C:54]=1[CH2:53][C:43]1[C:44]([CH2:51][CH3:52])=[N:45][C:46]2[C:41]([C:42]=1[O:62][CH3:63])=[C:40]([O:39][C@@H:37]([CH3:38])[C:36]([OH:64])=[O:35])[CH:49]=[CH:48][C:47]=2[F:50]

Participants

8

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 68780728HCID 68780728, compoundHCID 68781609HCID 68781609, compound

Product 2

HCID 16660248HCID 16660248, compoundHCID 57742507HCID 57742507, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of (S)-2-[3-(2,4-dichlorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]propionic acid methyl ester and (S)-2-[3-(2,4-dichlorobenzyl)-2-ethyl-8-fluoro-4-methoxyquinolin-5-yloxy]propionic acid methyl ester (0.58 g), methanol (10 mL), water (0.8 mL) and 5.0 M aqueous lithium hydroxide solution (0.40 mL) was stirred at room temperature overnight. The mixture was acidified by the addition of glacial acetic acid and concentrated under reduced pressure. Purification of the residue by column chromatography on C-18 column, eluting with a mixture of water and acetonitrile (4:1 to 0:1 by volume) gave (S)-2-[3-(2,4-dichlorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]propionic acid as a while solid, 0.23 and (S)-2-[3-(2,4-dichlorobenzyl)-2-ethyl-8-fluoro-4-methoxyquinolin-5-yloxy]propionic acid as a white solid, 0.035 g.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification of the residue by column chromatography on C-18 column
  3. washeluting with a mixture of water and acetonitrile (4:1 to 0:1 by volume)

Sources & evidence

ORD record
ord-f6f3c89c41e8463880b524c2d0623add
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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