Hydrochloric Acid → (S)-2-[(phenylisopropyl)amino]adenosine

Reaktionsgleichung

[C:1]1([CH:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[CH2:8]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:31](=O)(O)[O-].[Na+]>>[C:1]1([C:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])([CH3:8])[CH3:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

Edukt 3

HCID 313Hydrochloric Acid

HCID 516892Sodium Bicarbonate

HCID 53927112(R)-2-[(1-Phenylpropyl)amino]adenosine

Produkt 1

HCID 67681966(S)-2-[(phenylisopropyl)amino]adenosine

Versuchsvorschrift

Treat the secondary amine (3) (0.46 g, 1.05 mmol) with 1M hydrochloric acid (40 ml) and heat the reaction to 45° C. for 15 minutes. Cool the reaction and pour into saturated sodium bicarbonate (300 ml). Extract the reaction with chloroform (3×150 ml). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter, and concentrate under vacuum to provide the title compound (0.40 g) as the free base. Treat this with ethereal hydrogen chloride, filter, and dry the solid under high vacuum over phosphorous pentoxide. Recrystallize from 10% methanol/diethyl ether to provide, after drying under high vacuum over phosphorous pentoxide, the hydrochloride salt of the Formula I (184 mg), m.p. 155° C. dec.; [α]D20 =+9.75° (c=1.01, H2O).