Lithium hydroxide, monohydrate → HCID 66643592, compound

HRID 1923510Notes

Reaction equation

HRID 1923510 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:7][CH:6]=1)=[O:4].O.[OH-].[Li+]>C1COCC1.O>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:12]=1[CH2:11][CH2:10][C:8]1[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59568520HCID 59568520, compound

Product 1

HCID 66643592HCID 66643592, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-[2-(5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid methyl ester (835 mg, 2.54 mmol) in THF (8 mL) was added a solution of lithium hydroxide monohydrate (165 mg, 3.9 mmol) in water (8 mL) and the resulting mixture stirred at room temperature for 45 min. The mixture was then evaporated to half volume and then acidified to pH 1 with HCl (1N) and cooled to 0° C. for 15 min. A solid precipitated and was filtered off and dried to afford the title compound (769 mg, 96%) which was obtained as an off white solid. MS: m/e=314.1 [M−H]−.

Workup

  1. customThe mixture was then evaporated to half volume
  2. temperaturecooled to 0° C. for 15 min
  3. customA solid precipitated
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-74e56f6921c7478c99e28e154bcb7389
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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