反応式
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].CC(C)([O-])C.[K+].I[CH2:28][C@@H:29]([CH3:32])[CH2:30][CH3:31]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:20])[C@@H:5]([N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:28][CH:29]([CH3:32])[CH2:30][CH3:31])[CH3:2]参加物
反応条件
- 温度
- 0 °C
実験手順
A solution of (benzhydrylidene-amino)-acetic acid ethyl ester (5.48 g, 20.5 mmol) in tetrahydrofuran (40 mL) was treated with potassium t-butoxide (2.83 g, 25.26 mmol) and stirred at 0° C. for 35 min. At this time a solution of (S)-1-iodo-2-methyl-butane (5.00 g, 25.25 mmol) in tetrahydrofuran (20 mL) was added via syringe and the resulting solution stirred at 0° C. for 10 min and then room temperature overnight. The reaction mixture was concentrated in vacuo and the residue partitioned between diethyl ether and dilute aqueous hydrochloric acid. The layers were separated, and the organic layer was washed with brine and concentrated in vacuo. The residue was purified by ISCO flash chromatography (RediSep silica 120 g, 0% to 10% ethyl acetate/hexanes) which afforded (S)-2-(benzhydrylidene-amino)-4-methyl-hexanoic acid ethyl ester (5.09 g, 74%) as an oil.
後処理
- stirringthe resulting solution stirred at 0° C. for 10 min
- customroom temperature overnight
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue partitioned between diethyl ether and dilute aqueous hydrochloric acid
- customThe layers were separated
- washthe organic layer was washed with brine
- concentrationconcentrated in vacuo
- customThe residue was purified by ISCO flash chromatography (RediSep silica 120 g, 0% to 10% ethyl acetate/hexanes) which
出典と根拠
- ORDレコード
- ord-e2b1e4a3f0e64d58bf4a398c4d0d1a9d
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07741327B2
関連ノート
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