Methanol → 4-Methyl-2-[2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid

HRID 1923507Notes

Reaction equation

HRID 1923507 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([CH2:10][CH2:11][C:12]2[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:14][O:15][CH:16]=2)=[N:7][C:6]=1[CH3:23])=[O:4].O.[OH-].[Li+].CO>C1COCC1.O>[CH3:23][C:6]1[N:7]=[C:8]([CH2:10][CH2:11][C:12]2[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:14][O:15][CH:16]=2)[S:9][C:5]=1[C:3]([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 66643655HCID 66643655, compound

Product 1

HCID 666437194-Methyl-2-[2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-methyl-2-[2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid methyl ester (647 mg, 2.0 mmol) in THF (6.5 mL) was added a solution of lithium hydroxide monohydrate (165 mg, 3.9 mmol) in water (6.5 mL) followed by methanol (4 mL) and the resulting mixture stirred at room temperature for 4 h. The mixture was then evaporated to half volume and then acidified to pH 4 with HCl (1N) and cooled to 0° C. for 30 min. A solid precipitated and was filtered off and dried to afford the title compound (578 mg, 93%) which was obtained as a light brown solid. MS: m/e=314.1 [M−H]−.

Workup

  1. customThe mixture was then evaporated to half volume
  2. temperaturecooled to 0° C. for 30 min
  3. customA solid precipitated
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-4ff1f2aec9be46f995e8fbb8cbbfb431
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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