반응 #329987

반응 방정식

N-phenylbenzene-1,2-diamine

(S)-2-tertbutoxycarbonylaminobutyric acid

HOAt

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

4-methylmorpholine

→

[(S)-1-(1-Phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tertbutyl ester

수율 92.2%

용매

DCM

DCM

반응 조건

후처리

1. 1
   기타The crude reaction mixture
2. 2
   세척washed with a saturated solution of NaHCO3
3. 3
   건조dried (Na2SO4)
4. 4
   농축concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe resulting residue was dissolved in AcOH (20 mL)
6. 6
   온도heated to 70° C. for 18 h
7. 7
   온도After cooling to RT
8. 8
   기타volatiles were evaporated under reduced pressure
9. 9
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (150 mL)
10. 10
    세척washed with a saturated solution of NaHCO3
11. 11
    세척The organic layer was then washed with brine
12. 12
    건조dried (Na2SO4)
13. 13
    농축concentrated in vacuo
14. 14
    기타The resulting residue was absorbed onto HM-N
15. 15
    기타purified twice by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane)

실험 절차

A mixture of N-phenylbenzene-1,2-diamine (1.0 g, 5.43 mmol), (S)-2-tertbutoxycarbonylaminobutyric acid (1.21 g, 5.97 mmol), HOAt (813 mg, 5.97 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.15 g, 5.97 mmol) and 4-methylmorpholine (1.31 mL, 11.95 mmol) in DCM (20 mL) was stirred at RT for 2 h. The crude reaction mixture was diluted with DCM (100 mL), then washed with a saturated solution of NaHCO3, followed by brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was dissolved in AcOH (20 mL) and heated to 70° C. for 18 h. After cooling to RT, volatiles were evaporated under reduced pressure and the residue was dissolved in EtOAc (150 mL) and washed with a saturated solution of NaHCO3. The organic layer was then washed with brine, dried (Na2SO4) and then concentrated in vacuo. The resulting residue was absorbed onto HM-N and purified twice by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane) affording [(S)-1-(1-Phenyl-1H-benzoimidazol-2-yl)propyl]carbamic acid tertbutyl ester (1.76 g). LCMS: RT 3.23 min [M+H-tBu]+ 352.2

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