تفاعل #69130

معادلة التفاعل

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

D-Lactic Acid

diisopropylethylamine

TBTU

→

title compound

المردود 41.0%

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

المردود 41.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر