Acetic Acid → 1-({4-[3-(4-Isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylic acid

HRID 2247682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247682
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH2:21][N:22]4[CH2:25][CH:24]([C:26]([O:28]CC)=[O:27])[CH2:23]4)[S:19][CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].CO.C(O)(=O)C>O1CCOCC1.O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[C:18]([CH2:21][N:22]4[CH2:25][CH:24]([C:26]([OH:28])=[O:27])[CH2:23]4)[S:19][CH:20]=3)[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68525245Ethyl 1-({4-[3-(4-isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylate

Produkt 1

HCID 592180241-({4-[3-(4-Isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylic acidAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 1-({4-[3-(4-isobutylphenyl)isoxazol-5-yl]-2-thienyl}methyl)azetidine-3-carboxylate (0.47 g, 1.1 mmol) that was obtained in Example 9 (9h) in 1,4-dioxane (15 ml) was added a 1N aqueous solution of sodium hydroxide (3.3 ml, 3.3 mmol) at 0° C. with stirring, and then the resulting mixture was stirred at room temperature for 30 minutes. After adding methanol (15 ml) and water (5 ml) to the reaction mixture, the resulting mixture was heated under stirring until the white solid precipitated was dissolved, and then acetic acid (0.19 ml, 3.3 mmol) was added. The white solid precipitated was collected by filtration using a Kiriyama funnel, washed with methanol and dried in vacuo to afford the title compound (0.35 g) in a yield of 78% as a white crystalline solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. temperaturethe resulting mixture was heated
  3. stirringunder stirring until the white solid
  4. customprecipitated
  5. dissolutionwas dissolved
  6. customThe white solid precipitated
  7. filtrationwas collected by filtration
  8. washwashed with methanol
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5f56c01e3ac74179b718b38896e0463f
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687491B2

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