반응 #2015

반응 방정식

BOP

D-Tryptophan allyl ester

triethylamine

N-benzyloxycarbonyl-α-methylalanine

→

desired product

수율 84.5%

(R)-α-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, allyl ester

수율 84.5%

용매

—

hexanes

ethyl acetate

methylene chloride

반응 조건

후처리

1. 1
   기타the reaction quenched with saturated brine (5 ml)
2. 2
   기타The methylene chloride layer was separated
3. 3
   건조dried with magnesium sulfate
4. 4
   여과filtered
5. 5
   기타the volatiles removed under reduced pressure
6. 6
   기타to leave a dark brown oil

실험 절차

D-Tryptophan allyl ester (250 mg; 0.822 mmol), triethylamine (230 μl; 1.650 mmol) and N-benzyloxycarbonyl-α-methylalanine (167.9 mg; 0.826 mmol) were dissolved in dry methylene chloride (5 ml) and BOP (363.7 mg; 0.822 mmol) added. The reaction mixture was stirred at room temperature for 16 h and then the reaction quenched with saturated brine (5 ml). The methylene chloride layer was separated, dried with magnesium sulfate and filtered then the volatiles removed under reduced pressure to leave a dark brown oil. Chromatography of this oil on silica gel using ethyl acetate and hexanes 2:1 v/v afforded 322 mg (84.5%) of the desired product. FAB-MS:- calculated for C26H29N3O5 463.2; found 464.5 (M+1).

출처