Lithium Hydroxide → {3-[4-(1-Methyl-1H-pyrazol-4-yl)-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid

HRID 885371Notes

Reaction equation

HRID 885371 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)=[CH:15][C:14]=2[CH2:25][N:26]2[CH2:30][CH2:29][O:28][C:27]2=[O:31])[CH:7]=1)C.[OH-].[Li+]>COCCOC.O>[CH3:24][N:22]1[CH:23]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][C:8]3[CH:7]=[C:6]([CH2:5][C:4]([OH:32])=[O:3])[CH:11]=[CH:10][CH:9]=3)=[C:14]([CH2:25][N:26]3[CH2:30][CH2:29][O:28][C:27]3=[O:31])[CH:15]=2)[CH:20]=[N:21]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58237588HCID 58237588, compound

Product 1

HCID 58237474{3-[4-(1-Methyl-1H-pyrazol-4-yl)-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To the crude solution of {3-[4-(1-methyl-1H-pyrazol-4-yl)-2-(2-oxo-oxazolidin-3-ylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester (0.23 mmol) in DME and H2O was added lithium hydroxide (0.040 g, 0.95 mmol) in H2O (1 mL), and the reaction was stirred at 80° C. for 20 minutes. The mixture was acidified and concentrated, and the residue was dissolved in MeOH (4 mL) and purified by preparative HPLC to give the title compound.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in MeOH (4 mL)
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f8148aa5f4dc422387610d42b0105b5d
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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