1,1'-Carbonyldiimidazole → 4-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid methyl ester

HRID 1641820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1641820
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[CH3:13][O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([C:23](=[NH:26])[NH:24][OH:25])[CH2:19][CH2:18]1)=[O:16]>O1CCOCC1>[CH3:13][O:14][C:15]([CH:17]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:26][C:6](=[O:7])[O:25][N:24]=2)[CH2:19][CH2:18]1)=[O:16]

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178497951HCID 178497951, Verbindung

Produkt 1

HCID 1362068234-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid methyl esterAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of carbodiimidazole (624 mg, 3.85 mmol) and 4-(N-hydroxycarbamimidoyl)-cyclohexanecarboxylic acid methyl ester (770 mg, 3.85 mmol) in anhydrous 1,4 dioxane (15 mL) was heated in a sealed vial in an oil bath at 100° C. for 30 min. The reaction was concentrated, diluted with ethyl acetate (200 mL) washed with aqueous ammonium chloride (sat'd, 200 mL) and brine (200 mL), dried over sodium sulfate, and concentrated to give 4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid methyl ester (580 mg 67%) as a clear light yellow oil. LCMS calcd for C10H14N2O4 (m/e) 226, obsd 225 (M−H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate (200 mL)
  3. washwashed with aqueous ammonium chloride (sat'd, 200 mL) and brine (200 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-54226c381ed74d85bff65d411aa883c0
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08115011B2

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