Lithium hydroxide, monohydrate → HCID 66643727, compound

HRID 1923531Notes

Reaction equation

HRID 1923531 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][C:21]([F:24])=[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>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[C:12]([CH2:11][CH2:10][C:8]3[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=3)=[C:16]([CH3:17])[O:15][N:14]=2)=[N:19][CH:20]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66643620HCID 66643620, compound

Product 1

HCID 66643727HCID 66643727, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-ethyl}-thiazole-5-carboxylic acid methyl ester (1.27 g, 3.66 mmol) in THF (9 mL) was added a solution of lithium hydroxide monohydrate (307 mg, 7.31 mmol) in water (9 mL) and the resulting mixture stirred at room temperature for 2 h. The mixture was then evaporated to half volume and then acidified to pH 1 with HCl (1 N) and cooled to 0° C. for 15 min. A solid precipitated and was filtered off and dried to afford the title compound (707 mg, 58%) which was obtained as an off white solid after recrystallization from ethyl acetate. MS: m/e=332.3 [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-f8becba9a545439bae63fb9ff25cbb0c
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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