Hydrochloric Acid → Tert-butyl[4-chloro-2-(4-methyl-2-oxopentyl)phenyl]carbamate
反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:16])[CH:3]=1.[CH:17]([Li])(CC)C.O.Cl.[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[C:11]([O:10][C:9](=[O:15])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH2:16][C:28](=[O:24])[CH2:27][CH:26]([CH3:17])[CH3:25])([CH3:12])([CH3:13])[CH3:14]参加物
実験手順
To a solution of tert-butyl (4-chloro-2-methyphenyl)carbamate (483 mg) in tetrahydrofuran (7 mL) was added dropwise sec-butyllithium (1.04 mol/L hexane-cyclohexane solution, 4.3 mL) at −40° C. under an argon atmosphere, and the mixture was stirred for 15 minutes. Then a solution of N-methoxy-N,3-methylbutylamide (319 mg) in tetrahydrofuran (1 mL) was added dropwise, and the mixture was stirred at −40° C. for 15 minutes and at room temperature for 2 hours. Water and 1 mol/L hydrochloric acid were added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The aqueous layer was extracted once again with ethyl acetate. The combined organic layers were washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (282 mg).
後処理
- stirringthe mixture was stirred at −40° C. for 15 minutes and at room temperature for 2 hours
- extractionthis resulting mixture was extracted with ethyl acetate
- extractionThe aqueous layer was extracted once again with ethyl acetate
- washThe combined organic layers were washed with saturated saline
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)
出典と根拠
- ORDレコード
- ord-2677bf48b1ee41e2be9868d8c5d79de5
- 出典データセット
- uspto-grants-2014_03
- 特許番号
- US08680120B2
反応ノート
読み込み中…