1-[3-[[(Methylamino)thiocarbonyl]thio]propanoyl]-L-proline tertbutyl ester → 1-[3-[[(methylamino)thiocarbonyl]thio]propanoyl]-L-proline
Reaktionsgleichung
C([O:5][C:6](=[O:21])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:20])[CH2:13][CH2:14][S:15][C:16]([NH:18][CH3:19])=[S:17])(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[CH3:19][NH:18][C:16]([S:15][CH2:14][CH2:13][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:21])=[O:5])=[O:20])=[S:17]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
1-[3-[[(Methylamino)thiocarbonyl]thio]propanoyl]-L-proline tertbutyl ester (0.98 g) is dissolved in a mixture of anisole (3.6 ml) and trifluoroacetic acid (7.5 ml). After one hour at room temperature the mixture is concentrated to dryness in vacuo and the residue precipitated from ether-hexane three times. This material is chromatographed on a column of silica gel with a solvent mixture of benzene-acetic acid (75:25) to yield 1-[3-[[(methylamino)thiocarbonyl]thio]propanoyl]-L-proline, Rf = 0.4 [silica gel-benzene:acetic acid (75:25)]. The dicyclohexylammonium salt has m.p. 127°-129°.