(+)-L-Leucine methyl ester → (S)-2-{[6-(2-Methoxy-ethoxy)-5-piperidin-1-yl-pyrazine-2-carbonyl]-amino}-4-methyl-pentanoic acid methyl ester

Reaktionsgleichung

OC[C@@H](NC(C1C=NC(N2CCCC2)=C(OCCC)N=1)=O)CC(C)C.[CH3:26][O:27][CH2:28][CH2:29][O:30][C:31]1[N:36]=[C:35]([C:37]([OH:39])=O)[CH:34]=[N:33][C:32]=1[N:40]1[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1.[CH3:46][O:47][C:48](=[O:55])[C@H:49]([CH2:51][CH:52]([CH3:54])[CH3:53])[NH2:50]>>[CH3:46][O:47][C:48](=[O:55])[C@@H:49]([NH:50][C:37]([C:35]1[CH:34]=[N:33][C:32]([N:40]2[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]2)=[C:31]([O:30][CH2:29][CH2:28][O:27][CH3:26])[N:36]=1)=[O:39])[CH2:51][CH:52]([CH3:54])[CH3:53]

Komponenten

Edukt 3

HCID 65105(+)-L-Leucine methyl ester

HCID 248312586-Propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide

HCID 685690136-(2-Methoxy-ethoxy)-5-piperidin-1-yl-pyrazine-2-carboxylic acid

Produkt 1

HCID 24831736(S)-2-{[6-(2-Methoxy-ethoxy)-5-piperidin-1-yl-pyrazine-2-carbonyl]-amino}-4-methyl-pentanoic acid methyl ester

Versuchsvorschrift

In analogy to the procedure described for the synthesis of 6-propoxy-5-pyrrolidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide (example 10, step d) the title compounds was prepared from 6-(2-methoxy-ethoxy)-5-piperidin-1-yl-pyrazine-2-carboxylic acid and (S)-leucine methyl ester (commercially available). m/z (ES+): 409.3 (M+H).