Lithium hydroxide, monohydrate → 2-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acid

HRID 2381864Notes

Reaction equation

HRID 2381864 reaction equation
[F:1][C:2]([F:26])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[S:10][C:11]([C:15]([O:17]CC)=[O:16])=[C:12]([CH3:14])[N:13]=2)[N:6]=[N:5]1.O.[OH-].[Li+]>O1CCCC1.O>[F:26][C:2]([F:1])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[S:10][C:11]([C:15]([OH:17])=[O:16])=[C:12]([CH3:14])[N:13]=2)[N:6]=[N:5]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59179655ethyl 2-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 591797042-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(1-(2,2-difluoro-2-phenylethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate (0.13 g, 0.34 mmol) in a mixture of tetrahydrofuran (8 mL) and water (2 mL) was added lithium hydroxide monohydrate (0.05 g, 1.24 mmol). The reaction mixture was heated to reflux for 17 hours. The solvent was removed in vacuo, and the residue was neutralized to pH 4˜5 with 10% hydrochloric acid. The resulting precipitate was collected by filtration and dried to afford the title compound as a white solid (0.10 g, 84%): MS (ES+) m/z 349.1 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 17 hours
  3. customThe solvent was removed in vacuo
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-8489c8700e1b4a26a3e20b5947111095
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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