反応 #164500

反応方程式

1-bromo-3-methyl butane

N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

potassium carbonate

water

1-bromo-3-methyl butane

→

title compound

収率 68.0%

N-isoamyl-N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

収率 68.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGto stir for 16 h at ambient temperature
2. 2
   抽出extracted three times with dichloromethane
3. 3
   洗浄The combined organic extracts are washed with brine
4. 4
   乾燥dried over magnesium sulfate
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The crude product is purified by column chromatography
7. 7
   洗浄eluted with a gradient of 2-7% (hexanes-ethyl acetate)

実験手順

To a solution of N-(6-acetoxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (3.15 g, 7.48 mmol) in N,N-dimethylformamide (15 mL) is added potassium carbonate (3.09 g, 22.36 mmol), followed by 1-bromo-3-methyl butane (1.79 mL, 14.94 mmol), and the reaction is allowed to stir at ambient temperature for 16 h. Another equivalent of 1-bromo-3-methyl butane (0.9 mL, 7.5 mmol) is added and the reaction is allowed to stir for 16 h at ambient temperature. The reaction is poured over water and extracted three times with dichloromethane. The combined organic extracts are washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by column chromatography and eluted with a gradient of 2-7% (hexanes-ethyl acetate) to afford the title compound as a yellow oil (2.5 g, 68% yield), along with N-isoamyl-N-(6-(3-methylbutoxy)naphthalene-2-sulfonyl)-D-valine tert-butyl ester as a yellow oil (0.3 g, 7.7% yield). LCMS (m/z): (492.26; M+1).

出典