反应 #2015

反应方程式

BOP

D-Tryptophan allyl ester

triethylamine

N-benzyloxycarbonyl-α-methylalanine

→

desired product

收率 84.5%

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

收率 84.5%

溶剂

—

hexanes

ethyl acetate

methylene chloride

反应条件

后处理

1. 1
   其他the reaction quenched with saturated brine (5 ml)
2. 2
   其他The methylene chloride layer was separated
3. 3
   干燥dried with magnesium sulfate
4. 4
   过滤filtered
5. 5
   其他the volatiles removed under reduced pressure
6. 6
   其他to leave a dark brown oil

实验过程

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).

来源