Réaction #2013

Équation de réaction

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

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source