Water → {4-[4-(tert.-butoxy)-4-oxo-n-butyl]-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-acetic acid

HRID 660899Notes

Reaction equation

HRID 660899 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[N:13]([CH2:16][C:17]([O:19]C)=[O:18])[N:12]=[C:11]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].O>CO>[C:1]([O:5][C:6](=[O:28])[CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[N:13]([CH2:16][C:17]([OH:19])=[O:18])[N:12]=[C:11]1[C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58011851Methyl {4-[4-(tert.-butoxy)-4-oxo-n-butyl]-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-acetate

Product 1

HCID 58011723{4-[4-(tert.-butoxy)-4-oxo-n-butyl]-3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 48 mg (117 μmol) of the compound from Example 223A in 2 ml methanol is treated with a 1 N lithium hydroxide solution in water (470 μl, 470 μmol). After 1 hr at RT, the methanol is removed on the rotary evaporator. The residue is dissolved in DMSO and purified by preparative HPLC. 41 mg (88% of theory) of the title compound are obtained.

Workup

  1. customthe methanol is removed on the rotary evaporator
  2. dissolutionThe residue is dissolved in DMSO
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-b5a6263c6be0420992c49df5223b7fae
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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