Lithium Hydroxide → [3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

HRID 220691Notes

Reaction equation

HRID 220691 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:11](=[O:19])[N:10]([CH2:20][C:21]([O:23]C)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][C:15]([F:17])([F:16])[F:18])[C:11](=[O:19])[N:10]([CH2:20][C:21]([OH:23])=[O:22])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59536769Methyl [3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetate

Product 1

HCID 59536724[3-(4-Chlorophenyl)-5-oxo-4-(3,3,3-trifluoropropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Of the compound from Example 176A, 1.27 g (3.49 mmol), were introduced in 200 ml of methanol and 100 ml of water. Then 6.98 ml (6.98 mmol) of 1M aqueous lithium hydroxide solution were added. The mixture was stirred at RT for 2 h. For purification, 15 ml of 1N hydrochloric acid were added and the mixture was freed from methanol on a rotary evaporator. The residue was diluted with 100 ml of water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator, and dried in an HV. This gave 1.11 g (91% of theory) of the title compound.

Workup

  1. customFor purification, 15 ml of 1N hydrochloric acid
  2. additionwere added
  3. customthe mixture was freed from methanol on a rotary evaporator
  4. additionThe residue was diluted with 100 ml of water
  5. extractionextracted three times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. filtrationfiltered
  8. customfreed from the solvent on a rotary evaporator
  9. customdried in an HV

Sources & evidence

ORD record
ord-b8ba1ca66253479c82e6049f2b5b5106
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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