反应 #2011

反应方程式

BOP

amine

D-Homophenylalanine allyl ester

triethylamine

N-carbobenzyloxy-2-methylalanine

→

desired product

收率 69.7%

(R)-α-[(2-Benzyloxycarbonylamino-2-methyl-1-oxopropyl)amino]benzenebutanoic acid allyl ester

收率 69.7%

溶剂

methylene chloride

反应条件

后处理

1. 1
   其他the resultant homogenous yellow solution quenched by addition of brine
2. 2
   萃取The two phase system was extracted with methylene chloride (2×25 ml)
3. 3
   干燥the combined methylene chloride layers dried
4. 4
   过滤Filtration of the methylene chloride solution
5. 5
   其他to remove the
6. 6
   其他spent drying agent
7. 7
   其他followed by evaporation of solvent
8. 8
   其他afforded an oil which
9. 9
   其他was purified by column chromatography on silica gel using
10. 10
    workup.ADDITIONa solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant

实验过程

The amine obtained in Step B of this Example (300 mg; 1.37 mmol) triethylamine (380 ml; 2.73 mmol) and N-carbobenzyloxy-2-methylalanine (278 mg; 1.37 mmol) were dissolved in dry methylene chloride (3 ml) and BOP (605 mg; 1.37 mmol) was added. The reaction mixture was stirred at room temperature for 2 h and the resultant homogenous yellow solution quenched by addition of brine. The two phase system was extracted with methylene chloride (2×25 ml) and the combined methylene chloride layers dried over powdered anhydrous magnesium sulfate. Filtration of the methylene chloride solution to remove the spent drying agent followed by evaporation of solvent afforded an oil which was purified by column chromatography on silica gel using a solvent mixture of ethyl acetate and hexanes (1:1 v/v) as eluant. The desired product (419 mg; 69.7%) was isolated as a white amorphous solid. FAB-MS:- calculated for C25 H30N2O5 438.2; found 439.3 (M+1).

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