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

HRID 557743ノート

反応式

HRID 557743 の反応式
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]

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178497951HCID 178497951、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33351b3a6bec48bd82c07b9764ca3c36
出典データセット
uspto-grants-2011_11
特許番号
US08058299B2

反応ノート

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