반응 #329960

반응 방정식

N-Phenylbenzene-1,2-diamine

HOBt

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

4-methylmorpholine

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

(R/S)-2-tertbutoxycarbonylaminopropionic acid

racemic (R/S)-2-tertbutoxycarbonylaminopropionic acid

→

[1-(2-Phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester

수율 86.4%

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for further 4 h
2. 2
   기타The reaction mixture was then partitioned between water and EtOAc
3. 3
   기타The organic layer was separated
4. 4
   건조dried (MgSO4)
5. 5
   농축concentrated in vacuo
6. 6
   기타the resulting residue was purified by column chromatography (Si—PCC ISCO 24 g column, gradient 0-20% EtOAc in cyclohexane)
7. 7
   workup.ADDITIONThe product containing fractions
8. 8
   농축concentrated in vacuo

실험 절차

N-Phenylbenzene-1,2-diamine (1.84 g, 0.01 mol), racemic (R/S)-2-tertbutoxycarbonylaminopropionic acid (1.89 g, 0.01 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.92 g), 4-methylmorpholine (1.0 g, 0.01 mol), HOBt (1.53 g, 0.01 mol) were suspended in THF (10 mL) under a nitrogen atmosphere. The resulting mixture was stirred for 12 h at RT. After this period of time, additional amounts of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (500 mg×3) and of (R/S)-2-tertbutoxycarbonylaminopropionic acid (500 mg) were added and the mixture was stirred for further 4 h. The reaction mixture was then partitioned between water and EtOAc. The organic layer was separated, dried (MgSO4) and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC ISCO 24 g column, gradient 0-20% EtOAc in cyclohexane). The product containing fractions were combined and concentrated in vacuo affording [1-(2-Phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester as a white crystalline solid (3.07 g, 86%). LCMS: RT 3.61 min [M+H-tBu]+ 300.1.

출처