Hydrochloric Acid → [4-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid

HRID 456197Notes

Reaction equation

HRID 456197 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]2[CH2:28][CH2:27][O:26][C:25]2=[O:29])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[OH-].[Li+].Cl>O1CCOCC1.O>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:15][C:14]=2[CH2:23][N:24]2[CH2:28][CH2:27][O:26][C:25]2=[O:29])=[CH:6][C:5]=1[CH2:4][C:3]([OH:30])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66892534[4-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Product 1

HCID 44205511[4-Methoxy-2'-(2-oxo-oxazolidin-3-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To [4-methoxy-2′-(2-oxo-oxazolidin-3-ylmethyl)-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester (0.060 g, 1.42 mmol) in 1,4-dioxane:H2O (2:1; 2 mL) was added lithium hydroxide (14 mmol), and the reaction was stirred overnight at room temperature. The pH was adjusted to pH6 with 10% aqueous HCl, and the mixture was extracted with EtOAc. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound. M+H is 410.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f44677a17071443283a00101a5346916
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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