ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoate → (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one

HRID 2255666노트

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HRID 2255666 반응식
[Si:1]([O:8][C@H:9]([CH3:27])[C@H:10]([CH2:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:11](OCC)=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C=C(C)C=C(C)C=1[Mg]Br>O1CCCC1>[Si:1]([O:8][C@@H:9]([C@@H:10]1[CH2:16][N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:11]1=[O:12])[CH3:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 57031907ethyl (2S*,3R*)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoateHCID 178425415HCID 178425415, 화합물

생성물 1

HCID 54758409(3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one수율 50.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl (2S,3R)-3-(t-butyldimethylsilyloxy)-2-(4-methoxybenzylaminomethyl)butanoate (7.91 g, crude) in tetrahydrofuran (200 ml) was added dropwise mesitylmagnesium bromide (29 ml) at room temperature. After stirring for 30 minutes, the mixture was quenched with 0.2N hydrochloric acid (250 ml) ethyl acetate (200 ml). The aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layers were washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and an aqueous sodium chloride in turn, and then dried over magnesium sulfate. The resultant solution was evaporated, and the residue was purified by column-chromatography to give (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(4-methoxybenzyl)azetidin-2-one (3.55 g).

후처리

  1. customthe mixture was quenched with 0.2N hydrochloric acid (250 ml) ethyl acetate (200 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water
  5. dry with materialan aqueous sodium chloride in turn, and then dried over magnesium sulfate
  6. customThe resultant solution was evaporated
  7. customthe residue was purified by column-chromatography

출처 및 근거

ORD 기록
ord-a5a62cf226ea488290e804353440a542
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05241064

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