Lithium Hydroxide → (2-Chlorophenyl) [4-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,3-triazol-1-yl]acetic acid

HRID 714713Notes

Reaction equation

HRID 714713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:13]1[CH:17]=[C:16]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[C:21]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[N:20]2)[N:15]=[N:14]1)[C:9]([O:11]C)=[O:10].[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:13]1[CH:17]=[C:16]([CH2:18][N:19]2[C:23](=[O:24])[N:22]([CH2:25][C@H:26]([OH:31])[C:27]([F:30])([F:29])[F:28])[C:21]([C:32]3[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=3)=[N:20]2)[N:15]=[N:14]1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69940161Methyl (2-chlorophenyl)[4-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,3-triazol-1-yl]acetate

Product 1

HCID 69940366(2-Chlorophenyl) [4-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)-1H-1,2,3-triazol-1-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

49 mg (0.09 mmol) of the compound from Example 103 were dissolved in 2 ml of methanol, and 193 μl (0.19 mmol) of a 1 N aqueous lithium hydroxide solution were added. The mixture was stirred at RT for 30 min. The solvent was then removed under reduced pressure, the residue was dissolved in 5 ml of water and the solution was extracted once with 5 ml of ethyl acetate. The organic phase was discarded. The aqueous phase was acidified with 0.2 ml of 1 N hydrochloric acid and extracted twice with in each case 5 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave 40 mg (83% of theory) of the target compound.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue was dissolved in 5 ml of water
  3. extractionthe solution was extracted once with 5 ml of ethyl acetate
  4. extractionextracted twice with in each case 5 ml of ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20501ce455ff42528df93f288bdb13eb
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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