Lithium Hydroxide → HCID 16660087, compound

HRID 2266593Notes

Reaction equation

HRID 2266593 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl: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]([Cl:26])=[CH:22][C:21]=1[F:27])[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:6]([O:5][CH2:4][C:3]([OH:32])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[F:27])=[C:8]2[O:28][CH:29]([F:30])[F:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68784257HCID 68784257, compound

Product 1

HCID 16660087HCID 16660087, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [8-chloro-3-(4-chloro-2-fluorobenzyl)-4-difluoromethoxy-2-ethyl-quinolin-5-yloxy]acetic acid methyl ester (0.075 g), tetrahydrofuran (2.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.20 mL) was stirred at room temperature for 2 hour. The solvent was removed under reduced pressure and the residue diluted with water. The pH of mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and solvent removed under reduced pressure. The residue was crystallised from a mixture of acetonitrile and water to afford title compound, 0.057 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. additionThe pH of mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate and solvent
  6. customremoved under reduced pressure
  7. customThe residue was crystallised from a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-592715023b394b879112e807f77b72b2
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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