Hydrochloric Acid → {3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetic acid

HRID 574142Notes

Reaction equation

HRID 574142 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][N:5]1[C:9](=[O:10])[N:8](/[CH:11]=[CH:12]/[C:13]([F:16])([F:15])[F:14])[C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[N:6]1.[OH-].[Li+].Cl>CO.CS(C)=O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:7]2[N:8](/[CH:11]=[CH:12]/[C:13]([F:15])([F:14])[F:16])[C:9](=[O:10])[N:5]([CH2:4][C:3]([OH:24])=[O:2])[N:6]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59536880Methyl {3-(4-chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

Product 1

HCID 59536906{3-(4-Chlorophenyl)-5-oxo-4-[(1E)-3,3,3-trifluoroprop-1-en-1-yl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

260 mg (0.72 mmol) of the compound of Example 10A were dissolved in 5 ml of methanol, and 2.87 ml (2.87 mmol) of a 1M aqueous lithium hydroxide solution were added. The mixture was stirred at RT for 1 h and then acidified with 1N hydrochloric acid and diluted with DMSO. The entire solution was purified by preparative HLPC [Method 9]. This gave 215 mg (86% of theory) of the title compound.

Workup

  1. customThe entire solution was purified by preparative HLPC [Method 9]

Sources & evidence

ORD record
ord-465d3a3b598c4b89963259faf2ff5d82
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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