反応 #2008

反応方程式

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

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   その他to give a slightly cloudy solution
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 24 h
3. 3
   その他then quenched
4. 4
   workup.ADDITIONby adding saturated brine (10 ml)
5. 5
   抽出The two phase system was extracted with methylene chloride (2×25 ml)
6. 6
   乾燥the combined methylene chloride extracts dried over magnesium sulfate powder
7. 7
   ろ過filtered
8. 8
   その他evaporated on a rotary evaporator under reduced pressure
9. 9
   その他to give a cloudy, colorless oil
10. 10
    その他chromatographed on silica gel using an eluant
11. 11
    その他The product was isolated
12. 12
    その他after evaporation of the volatiles as a clear oil

実験手順

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).

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