Methanol → HCID 16659759, compound

HRID 2266547Notes

Reaction equation

HRID 2266547 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:28]([F:30])[F:29])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.CO.[OH-].[Na+]>C(O)(=O)C>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:9]2[C:10]([CH2:17][CH3:18])=[N:11][C:12]3[C:7]([C:8]=2[O:27][CH:28]([F:30])[F:29])=[C:6]([O:5][CH2:4][C:3]([OH:31])=[O:2])[CH:15]=[CH:14][C:13]=3[F:16])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68784662HCID 68784662, compound

Product 1

HCID 16659759HCID 16659759, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [3-(4-chlorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.11 g), methanol (10 mL), and 5.0 M aqueous sodium hydroxide solution (1.0 mL) was stirred at room temperature for 30 minutes. The pH of the solution was adjusted to 5 by the addition of glacial acetic acid. The solvent was removed under reduced pressured and the residue purified by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile in water (40% to 95% of organic modifier) to afford title compound as a white solid, 0.040 g.

Workup

  1. customThe solvent was removed
  2. customthe residue purified by preparative reverse-phase
  3. customover 30 minutes

Sources & evidence

ORD record
ord-ac9c033e2b5f449c8d6c6780a3309128
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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