Lithium Hydroxide → 4-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid

HRID 1641819ノート

反応式

HRID 1641819 の反応式
[OH-].[Li+].C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[NH:17][C:16](=[O:18])[O:15][N:14]=2)[CH2:9][CH2:8]1)=[O:6]>C1COCC1>[O:18]=[C:16]1[O:15][N:14]=[C:13]([CH:10]2[CH2:9][CH2:8][CH:7]([C:5]([OH:6])=[O:4])[CH2:12][CH2:11]2)[NH:17]1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 1362068234-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid methyl ester

生成物 1

HCID 1362068244-(5-Oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid収率 20%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of aqueous lithium hydroxide (215 mg, 5.13 mmol, 10 mL H20), 4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid methyl ester (580 mg, 2.56 mmol) and THF (40 mL) were stirred at room temperature for 5 hr. The reaction was then concentrated, diluted with aqueous sodium hydroxide (0.1 M, 100 mL) washed with ethyl acetate (100 mL). The basic solution was acidified with concentrated HCl and extracted with ethyl acetate (125 mL). The organic layer was washed with brine (100 mL), dried over sodium sulfate, concentrated, and dried from dichloromethane to give 4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclohexanecarboxylic acid (104 mg, 20%) as a white solid. LCMS calcd for C9H12N2O4 (m/e) 212, obsd 213 (M+H) and 211 (M−H).

後処理

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with aqueous sodium hydroxide (0.1 M, 100 mL)
  3. washwashed with ethyl acetate (100 mL)
  4. extractionextracted with ethyl acetate (125 mL)
  5. washThe organic layer was washed with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. dry with materialdried from dichloromethane

出典と根拠

ORDレコード
ord-5d35ad61e9cc491982376d1e9f4a82b1
出典データセット
uspto-grants-2012_02
特許番号
US08115011B2

反応ノート

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