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

HRID 557743노트

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HRID 557743 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-33351b3a6bec48bd82c07b9764ca3c36
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058299B2

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