3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-[(2-methylpropane-2-sulfinyl)imino]azetidine-1-carboxylate

HRID 509556

반응식

HRID 509556 반응식
O=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH3:13][C:14]([S:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[C:14]([S:17]([N:19]=[C:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1)=[O:18])([CH3:16])([CH3:15])[CH3:13]

참가 물질

5

반응물 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 3382465Tert-Butanesulfinamide

생성물 1

HCID 56776988tert-Butyl 3-[(2-methylpropane-2-sulfinyl)imino]azetidine-1-carboxylate수율 24%

시약·촉매·용매 2

HCID 178477244HCID 178477244, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

A mixture of tert-butyl 3-oxoazetidine-1-carboxylate (4 g, 23.37 mmol), 2-methylpropane-2-sulfinamide (3.12 g, 25.7 mmol) and tetraethoxytitanium (10.66 g, 46.7 mmol) in THF (40 ml) in a 20 ml sealed tube was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature, quenched with water and filtered through a bed of Celite. The solid material was washed with ethyl acetate. The organic layer was separated, dried over Na2SO4, filtered and concentrated to obtain a crude mixture. The crude product was then purified by column chromatography (20% EtOAc in Hexane) to afford tert-butyl 3-(tert-butylsulfinylimino)azetidine-1-carboxylate Yield: 1.5 g (24%). 1H NMR (400 MHz, CDCl3): δ 5.15-4.94 (m, 1H), 4.75 (m, 1H), 4.68 (s, 2H), 1.45 (s, 9H), 1.27 (s, 9H).

후처리

  1. customsealed tube
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched with water
  4. filtrationfiltered through a bed of Celite
  5. washThe solid material was washed with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto obtain a crude mixture
  11. customThe crude product was then purified by column chromatography (20% EtOAc in Hexane)

출처 및 근거

ORD 기록
ord-6457cae56dca409d9ce5a0a4b87ae24c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096580B2

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