Methanol → Melevodopa hydrochloride
Reaction equation
[O:1]=[C:2]([C@H:4]([CH2:6][C:7]1[CH:14]=[C:12]([OH:13])[C:10]([OH:11])=[CH:9][CH:8]=1)[NH2:5])[OH:3].S(Cl)([Cl:17])=O.[CH3:19]O>>[ClH:17].[CH3:19][O:1][C:2](=[O:3])[C@H:4]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:11])=[C:12]([OH:13])[CH:14]=1)[NH2:5]Participants
4
Procedure
A solution of 1.97 g (10 mmol) of L-DOPA 15 in 100 ml of MeOH at 0° C. was added 6.57 ml (90 mmol) of thionyl chloride via addition funnel. The mixture was stirred overnight while the temperature was slowly warmed to room temperature. The solvent was evaporated and the thick oil was treated with toluene (3×15 ml) and evaporated. The yield of white solid was 3.26 g (100%); NMR (DMSQ-d6) δ 2.90 (m, 2H), 3.38 (bs, 2H), 3.61 (s, 3H), 4.08 (m, 1H), 6.40 (d, 1H, J=7 Hz), 6.59 (s, 1H), 6.65(d, 2H, J=7 Hz), 8.59 (bs, 1H), 8.90 (d, 1H, J=10 Hz). MS: 212 m/z (M+H)+.
Workup
- addition