Lithium hydroxide, monohydrate → HCID 66643777, compound

HRID 1923521Notes

Reaction equation

HRID 1923521 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][C:6]=1[CH3:25])=[O:4].O.[OH-].[Li+]>C1COCC1.O.CO>[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])=[C:6]([CH3:25])[N:7]=3)=[C:16]([CH3:17])[O:15][N:14]=2)=[N:19][CH:20]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59568526HCID 59568526, compound

Product 1

HCID 66643777HCID 66643777, compoundYield 88.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-{2-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-ethyl}-4-methyl-thiazole-5-carboxylic acid methyl ester (1.02 g, 2.82 mmol) in THF (7 mL), water (7 mL) and MeOH (1.4 mL) was added lithium hydroxide monohydrate (237 mg, 5.65 mmol) and the resulting mixture stirred at room temperature overnight. 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 (867 mg, 88%) which was obtained as an off white solid. MS: m/e=346.2 [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-4587ce23fe8e4d2db58609710f63d5c5
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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