Citric Acid → HCID 58044110, 화합물

HRID 626760노트

반응식

HRID 626760 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 58044110HCID 58044110, 화합물수율 76%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-994071239e724523b840f6ce4850fd25
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

반응 노트

불러오는 중…