Methanol → HCID 136397837, compound

HRID 1836116Notes

Reaction equation

HRID 1836116 reaction equation
[CH:1]1([C:6]2[C:10]([NH:11][C:12](=O)[CH2:13][C:14]3[CH:19]=[CH:18][C:17](OC)=[CH:16]C=3)=[C:9]([C:23]([NH2:25])=[O:24])[O:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:26].[K+].[CH3:28]O>>[CH:1]1([C:6]2[C:10]3[N:11]=[C:12]([C:13]4[CH:14]=[CH:19][C:18]([O:26][CH3:28])=[CH:17][CH:16]=4)[NH:25][C:23](=[O:24])[C:9]=3[O:8][N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 23498798HCID 23498798, compound

Product 1

HCID 136397837HCID 136397837, compound

Procedure

2.56 g (7.45 mmol) of 3-cyclopentyl-4-{[2-(4-methoxyphenyl)acetyl]amino}-isoxazole-5-carboxamide (example X) are heated under reflux for 16 hours, together with 4.3 g of potassium hydroxide, in 170 ml of methanol. The solvent is removed in vacuo and the residue is taken up in dichloromethane; the solution is washed with 1N hydrochloric acid and water, after which the organic phase is dried over sodium sulfate and the solvent is removed. The residue is purified by chromatography (cyclohexane/ethyl acetate=2:1).

Workup

  1. customThe solvent is removed in vacuo
  2. washthe solution is washed with 1N hydrochloric acid and water
  3. dry with materialafter which the organic phase is dried over sodium sulfate
  4. customthe solvent is removed
  5. customThe residue is purified by chromatography (cyclohexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-683996ff8ffa4ab18ed0467f995900dc
Source dataset
uspto-grants-2004_08
Patent number
US06777416B2

Reaction notes

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