Реакция #69130

Уравнение реакции

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

D-Lactic Acid

diisopropylethylamine

TBTU

→

title compound

Выход 41.0%

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

Выход 41.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe crude mixture was partitioned between ethyl acetate and brine
2. 2
   СушкаThe organic extracts were dried over magnesium sulfate
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеThe residue was purified on silica gel by column chromatography (ISCO Companion, 12 g column, 0-10% MeOH/DCM)

Методика

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).

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