반응 #829329

반응 방정식

N-(((4-nitrophenyl)oxy)carbonyl)-L-valine methyl ester

2-isopropyl-4-(((N-methyl)amino)methyl)oxazole

→

desired compound

수율 54.1%

N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine Methyl Ester

수율 54.1%

용매

DMF

DMF

반응 조건

후처리

1. 1
   기타Solvent was removed by rotary evaporation in vacuo
2. 2
   기타the resulting oil dried on high vacuum for 1 hr
3. 3
   세척eluted with 20% EtOAc/CH2Cl2 and 3% MeOH/CH2Cl2
4. 4
   기타The material obtained after concentration of the product fractions
5. 5
   기타was repurified on a 100 g SiO2 flash column with a gradient of MeOH/CH2Cl2 (1%, 2%, 3%)

실험 절차

A solution of N-(((4-nitrophenyl)oxy)carbonyl)-L-valine methyl ester (0.903 g, 0.00305 mol) in anhydrous DMF (6 mL) was added to a solution of 2-isopropyl-4-(((N-methyl)amino)methyl)oxazole (9, 0.470 g, 0.00305 mol) in anhydrous DMF (6 mL) under argon, and the yellow solution was stirred at room temperature for 30 min. Solvent was removed by rotary evaporation in vacuo and the resulting oil dried on high vacuum for 1 hr. The residue was applied to a 150 g SiO2 flash column and eluted with 20% EtOAc/CH2Cl2 and 3% MeOH/CH2Cl2. The material obtained after concentration of the product fractions was repurified on a 100 g SiO2 flash column with a gradient of MeOH/CH2Cl2 (1%, 2%, 3%) to obtain the desired compound as an oil (0.515 g, 0.00165 mol, 54 %): 1H NMR (CDCl3)δ0.97 (dd, J1 =9 Hz, J2 =6.9 Hz, 6H), 1.33 (d, J=6.9 Hz, 6H), 2.11-2.23 (m, 1H), 2.98 (s, 3H), 3.00-3.13 (m, 1H), 3.77 (s, 3H), 4.23-4.36 (m, 2H), 4.36-4.42 (m, 1H), 5.79-5.86 (br d, 1H), 7.46 (s, 1H). Mass spectrum: (M+H)+ =312.

출처