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

HRID 424846Notes

Reaction equation

HRID 424846 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[N:21]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:35])[N:22]=[N:23][C:24]=3[CH:25]([CH3:27])[CH3:26])=[CH:14][C:13]=2[CH3:36])=[CH:6][CH:5]=1.[OH-].[Li+]>O1CCOCC1>[Cl:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([Cl:34])[C:28]=1[N:21]1[C:20]([CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]#[C:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=3)=[C:13]([CH3:36])[CH:14]=2)=[C:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[N:22]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 667041244-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenylethynyl}-benzoic acid methyl ester

Product 1

HCID 576527424-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy-]-2-methyl-phenylethynyl}-benzoic AcidYield 102.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an ambient temperature solution of 4-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenylethynyl}-benzoic acid methyl ester (32 mg, 0.0599 mmol) in dioxane (2 mL) is added a solution of lithium hydroxide (90 μL, 0.180 mmol, 2.0N in water). The reaction mixture is stirred at room temperature overnight. The reaction is concentrated and the residue is partitioned between Et2O and water. The aqueous layer pH is adjusted to approximately 4 and the aqueous layer 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 (32 mg, quant). LC-ES/MS m/e 520.2 (M+1), HPLC purity: 100%.

Workup

  1. concentrationThe reaction is concentrated
  2. customthe residue is partitioned between Et2O and water
  3. extractionthe aqueous layer is 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-ff47dc6cf9fa4d86b4e1d6eb3797f576
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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