Lithium Hydroxide → HCID 16659927, compound

HRID 2266579Notes

Reaction equation

HRID 2266579 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:28][CH:29]([F:31])[F:30])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[Cl:27])[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:27][C:21]1[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:20]=1[CH2:19][C:9]1[C:10]([CH2:17][CH3:18])=[N:11][C:12]2[C:7]([C:8]=1[O:28][CH:29]([F:30])[F:31])=[C:6]([O:5][CH2:4][C:3]([OH:32])=[O:2])[CH:15]=[CH:14][C:13]=2[F:16]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68781719HCID 68781719, compound

Product 1

HCID 16659927HCID 16659927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(2-chloro-4-fluorobenzyl)-4-difluoromethoxy-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (1.2 g), tetrahydrofuran (10 mL) and 1.0 M aqueous lithium hydroxide solution (3.0 mL) was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the pH of the residue adjusted to 4 by the addition of sodium dihydrogenphosphate. The mixture was extracted with ethyl acetate and the combined extracts dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound, 1.1 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe pH of the residue adjusted to 4 by the addition of sodium dihydrogenphosphate
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined extracts dried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-277b2dfd0420478ea91f21634789c26a
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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