반응 #2008

반응 방정식

BOP

D-Homophenylalanine benzyl ester

triethylamine

3-t-butoxycarbonylamino-3-methylbutanoic acid

→

(R)-α-[(3-t-Butoxycarbonylamino-3-methyl-1-oxobutyl)amino]benzenebutanoic acid benzyl ester

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   기타to give a slightly cloudy solution
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 24 h
3. 3
   기타then quenched
4. 4
   workup.ADDITIONby adding saturated brine (10 ml)
5. 5
   추출The two phase system was extracted with methylene chloride (2×25 ml)
6. 6
   건조the combined methylene chloride extracts dried over magnesium sulfate powder
7. 7
   여과filtered
8. 8
   기타evaporated on a rotary evaporator under reduced pressure
9. 9
   기타to give a cloudy, colorless oil
10. 10
    기타chromatographed on silica gel using an eluant
11. 11
    기타The product was isolated
12. 12
    기타after evaporation of the volatiles as a clear oil

실험 절차

D-Homophenylalanine benzyl ester (725 mg; 3.23 mmol) whose preparation was described in Example 7 Step B, triethylamine (750 ml; 5,38 mmol) and 3-t-butoxycarbonylamino-3-methylbutanoic acid (585 mg; 2.69 mmol) were dissolved in dry methylene chloride (10 ml) and BOP (1.19 g, 2.69 mmol) was added with stirring in small batches to give a slightly cloudy solution. The reaction mixture was stirred at room temperature for 24 h then quenched by adding saturated brine (10 ml). The two phase system was extracted with methylene chloride (2×25 ml) and the combined methylene chloride extracts dried over magnesium sulfate powder, filtered and evaporated on a rotary evaporator under reduced pressure to give a cloudy, colorless oil. This material was taken up in the minimum volume of methylene chloride and chromatographed on silica gel using an eluant composed of ethyl acetate and hexanes in the ratio 1:1 v/v. The product was isolated after evaporation of the volatiles as a clear oil. The yield was 710 mg (88.5%). FAB-MS: -calculated for C27H36N2 O5 468.3; found 469.6 (M+1).

출처