(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-oxopent-3-enyl)carbamate
反応式
[Si:1]([O:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22](N(OC)C)=[O:23])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]=[CH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:28]([Mg]Br)=[CH:29][CH3:30]>C1COCC1>[Si:1]([O:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22](=[O:23])[CH:28]=[CH:29][CH3:30])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18])[CH:11]=[CH2:12])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (Intermediate 5, 32.5 g, 80.73 mmol) in THF (400 mL) under nitrogen at 0° C. was added prop-1-enylmagnesium bromide (323 ml, 161.45 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 hour, then quenched with 400 mL 10% citric acid, diluted further with 100 mL water and extracted with ether. The organics were concentrated and the resulting oil was dissolved in ether and washed with water and brine. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (5%-20% ethyl acetate/hexanes) afforded the desired product as a colorless oil (27 g, 87%).
後処理
- customquenched with 400 mL 10% citric acid
- additiondiluted further with 100 mL water
- extractionextracted with ether
- concentrationThe organics were concentrated
- dissolutionthe resulting oil was dissolved in ether
- washwashed with water and brine
- dry with materialThe organics were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-053383a978ff41c59bf59e2a755af50c
- 出典データセット
- uspto-grants-2016_04
- 特許番号
- US09309245B2
反応ノート
読み込み中…