Potassium Hydroxide → HCID 73603515, compound

HRID 1774577Notes

Reaction equation

HRID 1774577 reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[C:12]=1[C:22]1[CH:23]=[CH:24][C:25]2[O:30][CH2:29][CH2:28][CH2:27][C:26]=2[CH:31]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([O:5][CH:6]([C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[C:12]=1[C:22]1[CH:23]=[CH:24][C:25]2[O:30][CH2:29][CH2:28][CH2:27][C:26]=2[CH:31]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 90096184HCID 90096184, compound

Product 1

HCID 73603515HCID 73603515, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-(1,3-thiazol-2-yl)-1H-pyrazol-5-yl]acetate (8h) (50 mg, 0.11 mmol) and potassium hydroxide (55 mg, 0.45 mmol) in a mixture of ethanol (1.0 mL) and water (1.0 mL) was refluxed overnight. The mixture was concentrated in vacuo. Water (2 mL) was added to the residue and the aqueous layer was washed with ethyl acetate (2 mL), acidified with 1M hydrochloric acid until pH 3 and extracted with ethyl acetate (2×3 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-(1,3-thiazol-2-yl)-1H-pyrazol-5-yl]acetic acid (example 8) (45 mg, 0.10 mmol, 93%).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. additionWater (2 mL) was added to the residue
  4. washthe aqueous layer was washed with ethyl acetate (2 mL)
  5. extractionextracted with ethyl acetate (2×3 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75bd365b81fb416c839bfb6a0e53c927
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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