Captopril → 1-[(2S)-3-[(3-(nitrooxy)propyl) carbonylthio]-2-methyl-1-oxopropyl]-L-proline
Reaktionsgleichung
[SH:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].FC1C([O:22][C:23](=O)[CH2:24][CH2:25][CH2:26][O:27][N+:28]([O-:30])=[O:29])=C(F)C(F)=C(F)C=1F>CN(C1C=CN=CC=1)C>[N+:28]([O:27][CH2:26][CH2:25][CH2:24][C:23]([S:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])=[O:22])([O-:30])=[O:29]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Using the same procedure described in Example 1 but starting from 1-[(2S)-3-mercapto-2-methyl-1-oxopropyl]-L-proline (Captopril)(0.41 g, 1.9 mmol), 4-(nitrooxy)butanoic acid pentafluorophenyl ester (0.60 g, 1.9 mmol) TEA (0.26 ml, 1.9 mmol) and DMAP (0.23 g, 1.9 mmol) after purification with Flash chromatography of the residue (CH2Cl2/Acetone 80:20) the title compound (0.140 g, 20%) was obtained as a white foam.