反応 #2013

反応方程式

BOP

D-Homophenylalanine allyl ester

triethylamine

4-(benzyloxycarbonylamino)-4-methyl-pentanoic acid

→

(R)-α-[(4-Benzyloxycarbonylamino-4-methyl-1-oxopentyl)amino]benzenebutanoic acid allyl ester

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   workup.STIRRINGthis reaction mixture stirred at room temperature for 17 h
2. 2
   その他The reaction was quenched
3. 3
   workup.ADDITIONby adding brine
4. 4
   その他the products of the reaction isolated by extraction with methylene chloride (3×15 ml)
5. 5
   乾燥dried with anhydrous magnesium sulfate powder
6. 6
   ろ過filtered
7. 7
   その他evaporated under reduced pressure
8. 8
   その他A thick golden yellow gum was obtained which
9. 9
   その他was purified by column chromatography on silica gel
10. 10
    その他The product (182 mg; 48.9%) was isolated as a pale yellow gum

実験手順

D-Homophenylalanine allyl ester (175 mg; 0.80 mmol) (see Example 9, Step B), triethylamine (222 μl; 1.59 mmol) were dissolved in dry methylene chloride (2 ml) and 4-(benzyloxycarbonylamino)-4-methyl-pentanoic acid (211 mg; 0.80 mmol) added. The solution was stirred at room temperature and BOP (353 mg; 0.80 mmol) was added over 5 minutes, and this reaction mixture stirred at room temperature for 17 h. The reaction was quenched by adding brine and then the products of the reaction isolated by extraction with methylene chloride (3×15 ml). The methylene chloride layers were combined and dried with anhydrous magnesium sulfate powder, filtered and evaporated under reduced pressure. A thick golden yellow gum was obtained which was purified by column chromatography on silica gel using ethyl acetate and hexanes 1:2 v/v. The product (182 mg; 48.9%) was isolated as a pale yellow gum. FAB-MS:- calculated for C27H34 N2O5 466.3; found 467.7 (M+1).

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