1-(3-Acetylthiopropanoyl)-L-proline → 1-(3-Mercapto-1-oxopropyl)-L-proline
Reaction equation
C([S:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8])(=O)C>N>[SH:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])=[O:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
1-(3-Acetylthiopropanoyl)-L-proline (0.8 g.) is dissolved in 5.5 N methanolic ammonia (5 ml.) and the solution kept under argon at room temperature. After 2 hours the solvent is removed in vacuo, the residue is dissolved in water and applied to an ion exchange column on the H+ cycle [Dowex 50 (Analytical grade)] and eluted with water. The fractions that give thiol positive reaction are pooled and concentrated to dryness, yield 0.6 g. This product is crystallized from ethyl acetate-hexane as in Procedure A to obtain 1-(3-mercaptopropanoyl)-L-proline.
Workup
- customkept under argon at room temperature