Sodium Iodide → 1-[(2S)-3-(4-iodobutoxycarbonyl) mercapto-2-methyl-1-oxopropyl]-L-proline
Reaktionsgleichung
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([S:9][CH2:10][C@@H:11]([CH3:22])[C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])=[O:8].[Na+].[I-:24]>CC#N>[I:24][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]([S:9][CH2:10][C@@H:11]([CH3:22])[C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])=[O:8]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
1-[(2S)-3-(4-chlorobutoxycarbonyl)mercapto-2-methyl-1-oxopropyl]-L-proline (5.80 g, 0.0157 Mol) was dissolved in CH3CN (100 ml) and NaI (23.9 g, 0.160 Mol) was added to the solution. The mixture was refluxed for 7 h, then concentrated and diluted with CH2Cl2. The solid formed was filtered off and the organic phase was washed with H2O (3×50 ml), dried over sodium sulphate and evaporated under reduced pressure affording 1-[(2S)-3-(4-iodobutoxycarbonyl) mercapto-2-methyl-1-oxopropyl]-L-proline (7.10 g) as an oil that was used without further purification.