反応 #69130

反応方程式

Trans-tert-butyl (R)-1-(4-aminocyclohexyl)ethylcarbamate

D-Lactic Acid

diisopropylethylamine

TBTU

→

title compound

収率 41.0%

Trans-tert-butyl (R)-1-(4-((R)-2-hydroxypropanamido)cyclohexyl)ethylcarbamate

収率 41.0%

溶媒

DMF

反応条件

後処理

1. 1
   その他The crude mixture was partitioned between ethyl acetate and brine
2. 2
   乾燥The organic extracts were dried over magnesium sulfate
3. 3
   ろ過filtered
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The residue was purified on silica gel by column chromatography (ISCO Companion, 12 g column, 0-10% MeOH/DCM)

実験手順

Trans-tert-butyl (R)-1-(4-aminocyclohexyl)ethylcarbamate (125 mg, 0.52 mmol) was dissolved in DMF (3 mL). D-Lactic Acid (49.52 mg, 0.52 mmol), diisopropylethylamine (166.6 mg, 224.5 μL, 1.29 mmol) and TBTU (165.6 mg, 0.5158 mmol) were successively added. The reaction mixture was allowed to stir at ambient temperature for 3 hours. The crude mixture was partitioned between ethyl acetate and brine. The organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by column chromatography (ISCO Companion, 12 g column, 0-10% MeOH/DCM) to afford the title compound (66.1 mg, 41% yield).

出典