Acetic Acid → HCID 86645984, compound

Participants

Reaction Steps

To a cooled (0-5° C.) solution of potassium cyanide (0.2 g, 3.66 mmol) in water (15 ml) (2R)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanal (1.0 g, 3.33 mmol) (prepared according the procedure described for intermediate 7b and starting from the corresponding propanoate) was added over 30 min. At the same temperature AcOH (3.66 mmol) was dripped and the reaction mixture stirred for 18 h. The solution of the intermediate cyanohydrin was slowly added to another solution of NH4Cl (0.5 g, 9.66 mmol) in NH4OH (14N in H2O; 4.0 mmol) (5 ml). The resulting reaction mixture was stirred at room temperature for 18 h and then extracted with CH2Cl2 (3×15 ml). The organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum to give (3R)-2-amino-3-{4-[(4-(trifluoromethyl)-1,3-thiazol-2-yl)amino]phenyl}butanenitrile (0.705 g, 2.16 mmol) as red oil, used for the next step without further purification. 1H-NMR (DMSO-d6): δ 9.25 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.00 (s, 1H), 5.00 (s, 1H), 3.90 (q, 1H, J=7 Hz), 2.35 (bs, 2H), 1.75 (d, 3H, J=7 Hz).

Provenance & Evidence