Reaktion #6581

Reaktionsgleichung

hydrochloric acid

N-[{1-[(2-Chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methyl]phenylalanine methyl ester

formaldehyde

→

N-[{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol -5-yl}methyl]-N-methylphenylalanine methyl ester

Ausbeute 70.4%

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with diethyl ether
2. 2
   Extraktionthe product was extracted into ethyl acetate
3. 3
   ExtraktionThe organic extract
4. 4
   Trocknenwas dried with anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was removed in vacuo
6. 6
   SonstigeThe crude product was chromatographed on silica gel with 50% ethyl acetate in hexane

Vorschrift

N-[{1-[(2-Chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methyl]phenylalanine methyl ester (prepared in Example 3(i) method B) (o.52 g, 1.18 mmol), 88% formic acid (0.31 g), and 37% aqueous formaldehyde (o.44 g) were heated over a steam bath for 18 hours. The reaction mixture was poured into 10% hydrochloric acid solution and then extracted with diethyl ether. The aqueous layer was basified to pH 10 with 10% sodium hydroxide solution and then the product was extracted into ethyl acetate. The organic extract was dried with anhydrous magnesium sulfate and the solvent was removed in vacuo. The crude product was chromatographed on silica gel with 50% ethyl acetate in hexane to give 0.377 g (70%) of N-[{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol -5-yl}methyl]-N-methylphenylalanine methyl ester. Hydrolysis of the ester following the procedure of Example 2(ii) gave the title compound as a foam (0.265 g, 77%); mp 59°-61° C.

Quelle