Citric Acid → HCID 58044110、化合物

HRID 626760ノート

反応式

HRID 626760 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:13]=[N:14][C:15]([N:18]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:16][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]2[CH:13]=[N:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 311Citric AcidHCID 86697066tert-Butyl 3-(6-(Diphenylmethyleneamino)pyridin-3-yl)azetidine-1-carboxylate

生成物 1

HCID 58044110HCID 58044110、化合物収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-[6-(benzhydrylideneamino)-pyridin-3-yl]-azetidine-1-carboxylic acid tert-butyl ester (400 mg, 0.97 mmol) in THF (20 mL) was added citric acid (10 mL, 10% aqueous) and the reaction mixture was stirred at room temperature overnight. The resultant mixture was quenched by adding sodium hydrogen carbonate solution and was then extracted with ethyl acetate (×2). The combined organic washings were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (70-100% ethyl acetate in cyclohexane) to afford the title compound as a white solid (183 mg, 76%). LCMS (Method C): RT=1.85 min, m/z: 250 [M+H+].

後処理

  1. customThe resultant mixture was quenched
  2. additionby adding sodium hydrogen carbonate solution
  3. extractionwas then extracted with ethyl acetate (×2)
  4. washThe combined organic washings were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash chromatography (70-100% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-994071239e724523b840f6ce4850fd25
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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