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

HRID 2255666ノート

反応式

HRID 2255666 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a5a62cf226ea488290e804353440a542
出典データセット
uspto-grants-1993_08
特許番号
US05241064

反応ノート

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