반응 #80969

반응 방정식

4-nitrophenyl chloroformate

L-valine methyl ester hydrochloride

4-methylmorpholine

→

desired compound

N-(((4-Nitrophenyl)oxy)carbonyl)-L-valine Methyl Ester

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.ADDITIONThe resulting mixture was treated slowly
2. 2
   세척After washing with 3 portions of 10% aqueous NaHCO3
3. 3
   건조the solution was dried over Na2SO4
4. 4
   농축concentrated in vacuo
5. 5
   기타The residue was purified by silica gel chromatography
6. 6
   세척by eluting with chloroform

실험 절차

A solution of 66.1 g (0.328 mol) of 4-nitrophenyl chloroformate in 1.2 liters of CH2Cl2 was cooled to 0° C. and treated with L-valine methyl ester hydrochloride. The resulting mixture was treated slowly, with stirring, with 68.9 ml (0.626 mol) of 4-methylmorpholine. The resulting solution was allowed to slowly warm to ambient temperature and was stirred overnight. After washing with 3 portions of 10% aqueous NaHCO3, the solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography by eluting with chloroform to provide the desired compound. 1H NMR (DMSO-d6) δ0.94 (d, J=7 Hz, 3H), 0.95 (d, J=7 Hz, 3H), 2.12 (octet, J=7 Hz, 1H), 3.69 (s, 3H), 4.01 (dd, J=8, 6 Hz, 1H), 7.41 (dt, J=9, 3 Hz, 2H), 8.27 (dt, J=9, 3 Hz, 2H), 8.53 (d, J=8 Hz, 1H). Mass spectrum: (M+NH4)+ =314.

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