Reaktion #2009

Reaktionsgleichung

N-(t-Butoxycarbonyl)-D-homophenylalanine

allyl alcohol

EDC

→

N-(t-Butoxycarbonyl)-D-homophenylalanine allyl ester

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred at room temperature for 6 h
2. 2
   SonstigeThe reaction was quenched
3. 3
   workup.ADDITIONby pouring the reaction mixture into water (10 ml)
4. 4
   Extraktionextracted with methylene chloride (2×25 ml)
5. 5
   WaschenThe combined methylene chloride extracts were washed successively with 5% aqueous citric acid solution (50 ml)
6. 6
   TrocknenThe methylene chloride layer was dried over anhydrous magnesium surf
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto leave a thick oily residue which
10. 10
    Sonstigewas purified by column chromatography on silica gel using an eluant comprising ethyl acetate and hexanes in the ratio 2:1

Vorschrift

N-(t-Butoxycarbonyl)-D-homophenylalanine (2.0 g; 7.16 mmol), allyl alcohol (500 ml; 7.35 mmol) and 4-dimethylaminopyridine (88 mg; 0.72 mmol) were dissolved in dry methylene chloride and stirred at room temperature. EDC (1.4 g; 7.30 mmol) was added to the solution in small batches over 15 minutes and the reaction mixture stirred at room temperature for 6 h. The reaction was quenched by pouring the reaction mixture into water (10 ml) and extracted with methylene chloride (2×25 ml). The combined methylene chloride extracts were washed successively with 5% aqueous citric acid solution (50 ml) and a 10% aqueous sodium carbonate solution. The methylene chloride layer was dried over anhydrous magnesium surf ate powder, filtered and evaporated to leave a thick oily residue which was purified by column chromatography on silica gel using an eluant comprising ethyl acetate and hexanes in the ratio 2:1. The yield of the desired allyl ester product was 1.96 g (85.7%). FAB-MS:- calculated for C18 H25NO4 319.2; found 320. (M+1).

Quelle