Lithium Hydroxide → HCID 16660245, compound

HRID 2266618Notes

Reaction equation

HRID 2266618 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:33][CH:34]([F:36])[F:35])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])=[CH:22][CH:21]=1)[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:37])=[O:2])=[C:7]2[C:12]=1[N:11]=[C:10]([CH2:17][CH3:18])[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)=[O:27])=[CH:24][CH:25]=1)=[C:8]2[O:33][CH:34]([F:35])[F:36]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68782694HCID 68782694, compound

Product 1

HCID 16660245HCID 16660245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {8-chloro-4-difluoromethoxy-2-ethyl-3-[4-(pyrrolidine-1-carbonyl)benzyl]quinolin-5-yloxy}acetic acid methyl ester (0.037 g), tetrahydrofuran (3.0 mL) and 1.0 M aqueous lithium hydroxide solution (1.0 mL) was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure, acidified by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and the solvent removed under reduced pressure to afford title compound, 0.034 g.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionacidified by the addition of sodium dihydrogenphosphate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5a5ce6bff66f4ad6997fef18df955de0
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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