Water → 4-{[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoic acid

HRID 536547Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[CH:30][CH:31]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

An amount of 280 mg (0.61 mmol) of the compound from Example 24A was dissolved in 4 ml of a 1:1 mixture of methanol and THF and admixed with 0.61 ml of 2 N sodium hydroxide solution. It was stirred at 80° C. for 1 h. For working out, it was admixed with 5 ml of water and extracted with 5 ml of ethyl acetate. The aqueous phase was acidified to a pH of 1 using 1 N hydrochloric acid and extracted with twice 5 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. This gave 275 mg (100% of theory) of the target compound.

Workup

extractionextracted with 5 ml of ethyl acetate
extractionextracted with twice 5 ml of ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulphate
customfreed from the solvent on a rotary evaporator

Sources & evidence

ORD record: ord-4f8285b3f478495f9df47cbe1f00b928
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859601B2

Reaction notes

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