Lithium Hydroxide → 3-(1-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethylsulfanyl)-benzoic Acid

HRID 424829Notes

Reaction equation

HRID 424829 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[N:22]([C:29]4[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:36])[N:23]=[N:24][C:25]=3[CH:26]([CH3:28])[CH3:27])=[CH:15][C:14]=2[CH3:37])[CH3:12])[CH:5]=1.[OH-].[Li+]>O1CCOCC1>[Cl:36][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([Cl:35])[C:29]=1[N:22]1[C:21]([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH:11]([S:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:38])=[O:2])[CH3:12])=[C:14]([CH3:37])[CH:15]=2)=[C:25]([CH:26]([CH3:28])[CH3:27])[N:24]=[N:23]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 667041173-(1-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethylsulfanyl)-benzoic acid methyl ester

Product 1

HCID 576527403-(1-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethylsulfanyl)-benzoic AcidYield 94.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To an ambient temperature solution of 3-(1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethylsulfanyl)-benzoic acid methyl ester (53 mg, 0.0934 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (140 μL, 0.280 mmol, 2.0N in water). The reaction is heated to 50° C. for 2 h. The reaction mixture is concentrated and the residue is diluted with Et2O and water. The aqueous layer is adjusted to pH ˜4 and is extracted with a second portion of Et2O. The combined organic layers are washed with water, dried (MgSO4), filtered, and concentrated to yield the title compound (49 mg, 94%). LC-ES/MS m/e 556.3 (M+1), HPLC purity: 100%.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionthe residue is diluted with Et2O and water
  3. extractionis extracted with a second portion of Et2O
  4. washThe combined organic layers are washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6a2f90e877824934b758e3540bfac4d5
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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