Acetic Acid → 1-({5-[5-(4-Cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylic acid

HRID 2247643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2247643
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23][N:24]5[CH2:27][CH:26]([C:28]([O:30]CC)=[O:29])[CH2:25]5)=[CH:20][CH:19]=4)[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.O.[OH-].[Li+].C(O)(=O)C>O.CO>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23][N:24]5[CH2:27][CH:26]([C:28]([OH:30])=[O:29])[CH2:25]5)=[CH:20][CH:19]=4)[N:14]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68524364HCID 68524364, Verbindung

Produkt 1

HCID 119778161-({5-[5-(4-Cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylic acidAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of ethyl 1-({5-[5-(4-cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methyl)azetidine-3-carboxylate (0.23 g, 0.53 mmol) that was obtained in Example 2 (2d) in a mixed solvent of tetrahydrofuran (0.50 ml), methanol (0.50 ml) and water (0.50 ml) was added lithium hydroxide monohydrate (50 mg, 1.2 mmol) with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, acetic acid (65 μl, 1.2 mmol) was added to the reaction mixture to quench the reaction. The white solid precipitated was collected by filtration using a Kiriyama funnel, washed with a mixed solvent of water and methanol (3:7) and dried in vacuo to afford the title compound (122 mg) in a yield of 56% as a white crystalline solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. stirringAfter stirring
  3. customto quench
  4. customthe reaction
  5. customThe white solid precipitated
  6. filtrationwas collected by filtration
  7. washwashed with a mixed solvent of water and methanol (3:7)
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-79546d31bb11429d8d3129d7ea71e82d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687491B2

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