Lithium hydroxide, monohydrate → 2-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid

HRID 1882476Notes

Reaction equation

HRID 1882476 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]2[C:10](=[O:11])[N:9]([C:12]3[S:13][C:14]([C:18]([O:20]CC)=[O:19])=[C:15]([CH3:17])[N:16]=3)[CH:8]=[N:7]2)[CH2:3][CH2:2]1.O.[OH-].[Li+]>O1CCCC1.O>[CH:1]1([CH2:4][CH2:5][N:6]2[C:10](=[O:11])[N:9]([C:12]3[S:13][C:14]([C:18]([OH:20])=[O:19])=[C:15]([CH3:17])[N:16]=3)[CH:8]=[N:7]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66661569ethyl 2-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 666614672-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate (0.20 g, 2.78 mmol) in tetrahydrofuran (10 mL) and water (5 mL) was added lithium hydroxide monohydrate (0.15 g, 3.11 mmol) at ambient temperature. The resulting reaction mixture was heated to reflux for 20 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 2-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid in 55% yield (0.10 g): MS (ES−) m/z 293.1 (M−1).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 20 hours
  4. customThe solvent was removed in vacuo
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-80558d83ec4a42aab030abd18ffddd79
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

Loading…