Hydrogen Peroxide → Tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate

HRID 1867739노트

반응식

HRID 1867739 반응식
[OH-:1].[Na+].[CH2:3]([N:10]([CH3:20])[C:11]1([C:18]#[N:19])[CH2:14][N:13]([C:15]([O-:17])=[O:16])[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.OO>C(O)C>[NH2:19][C:18]([C:11]1([N:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:20])[CH2:14][N:13]([C:15]([O:17][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:16])[CH2:12]1)=[O:1]

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 866169483-[Benzyl(methyl)amino]-3-cyanoazetidine-1-carboxylate

생성물 1

HCID 69048045Tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate수율 165.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A 1M solution of sodium hydroxide (12.5 ml, 12.5 mmol) at 0° C. was added dropwise to a solution of 3-[benzyl(methyl)amino]-3-cyanoazetidine-1-carboxylate (800 mg, 2.66 mmol) in ethanol (25 ml). Hydrogen peroxide 30% wt (1 ml) was then added and the reaction mixture was allowed to stir at room temperature overnight. After removal of solvent under reduced pressure, the remaining aqueous layer was extracted with ethyl acetate (×2) and the combined organic layers washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl 3-(aminocarbonyl)-3-[benzyl(methyl)amino]azetidine-1-carboxylate (702 mg, 87%) as a white solid, used without any further purification in the next step; 1H NMR Spectrum: (CDCl3) 1.45 (s, 9H), 2.27 (s, 3H), 3.61 (s, 2H), 4.07 (d, 2H), 4.22 (brd, 2H), 5.51 (brs, 1H), 6.70 (brs, 1H), 7.26-7.36 (m, 5H); Mass Spectrum: (M+H)+ 320.

후처리

  1. customAfter removal of solvent under reduced pressure
  2. extractionthe remaining aqueous layer was extracted with ethyl acetate (×2)
  3. washthe combined organic layers washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cb274ce43a55455c9e44b43b88b36447
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632840B2

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