2,3-Dihydroxybutanedioic Acid → (S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

反応式

[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[C:23]([C@H:26]([C@@H:28]([C:30]([O-:32])=[O:31])[OH:29])[OH:27])([O-:25])=[O:24].C(O)(=O)C(C(C(O)=O)O)O.C(C(C(C([O-])=O)O)O)([O-])=O.[NH4+].[NH4+]>>[CH3:1][N:2]([CH2:4][CH2:5][C@H:6]([O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:3].[C:23]([C@H:26]([C@@H:28]([C:30]([O-:32])=[O:31])[OH:29])[OH:27])([O-:25])=[O:24]

参加物

反応物 3

HCID 8752,3-Dihydroxybutanedioic Acid

HCID 2724224Diammonium tartrate

HCID 86625060N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

生成物 1

HCID 86625059(S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine D-tartrate

実験手順

first by converting it to a mixture of diastereoisomeric salts of N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine/D-tartrate via reaction with optically active tartaric acid in the molar ratio 1:2 relative to the substance of formula III or with optically active alkali metal tartrate or ammonium tartrate, or an alkylammonium tartrate, of formula IV, in the molar ratio 1:1, followed by isolating the salt (S)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine/D-tartrate (2:1) (Scheme 2) from the mixture of the diastereoisomeric salts in an organic solvent, water or a mixture thereof.