Lithium hydroxide, monohydrate → HCID 67958635, compound

HRID 72478Notes

Reaction equation

HRID 72478 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([O:7][CH:8]2[CH2:11][N:10]([C:12]3[N:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:13]=3[C:14]([O:16]C)=[O:15])[CH2:9]2)[CH:3]=1.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([O:7][CH:8]2[CH2:11][N:10]([C:12]3[N:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][C:13]=3[C:14]([OH:16])=[O:15])[CH2:9]2)[CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67958466Methyl 2-(3-((5-methylisoxazol-3-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinate

Product 1

HCID 67958635HCID 67958635, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of methyl 2-(3-((5-methylisoxazol-3-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinate (D88) (20 mg, 0.056 mmol) in 1,4-dioxane/water (3 ml/1 ml), lithium hydroxide monohydrate (3.52 mg, 0.084 mmol) and the resulting mixture was heated at 130° C. under microwave irradiation 10 min (2 cycles of 5 min each). Solvents were evaporated in vacuo and the residue was taken in a mixture water/1M HCl (5 ml/15 ml) and extracted with ethyl acetate (3×20 ml). Collected organics, after solvent evaporation, afforded the title compound (D129) (19 mg)

Workup

  1. customSolvents were evaporated in vacuo
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. customCollected organics, after solvent evaporation

Sources & evidence

ORD record
ord-7fe44e1d29b644e7a4d896c353aad76c
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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