Sodium Hydroxide → Aliskiren
Reaction equation
[OH-].[Na+].Cl.[C:4]([C:7]([CH3:42])([CH3:41])[CH2:8][NH:9][C:10](=[O:40])[C@H:11]([CH:37]([CH3:39])[CH3:38])[CH2:12][C@H:13]([OH:36])[C@@H:14]([NH2:35])[CH2:15][C@@H:16]([CH:32]([CH3:34])[CH3:33])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=1)(=[O:6])[NH2:5]>O>[C:4]([C:7]([CH3:42])([CH3:41])[CH2:8][NH:9][C:10](=[O:40])[C@H:11]([CH:37]([CH3:38])[CH3:39])[CH2:12][C@H:13]([OH:36])[C@@H:14]([NH2:35])[CH2:15][C@@H:16]([CH:32]([CH3:34])[CH3:33])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:19]=1)(=[O:6])[NH2:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
20 g of ice and 12 ml of 2N NaOH are added in succession to a stirred solution of 2.35 g of 5(S)-amino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid N-(2-carbamoyl-2,2-dimethyl-ethyl)-amide hydrochloride (Example 137) in 20 ml of water, and the mixture is then extracted with 3×50 ml of tertbutyl methyl ether. The combined organic phases are dried with magnesium sulfate and concentrated by evaporation. 0.232 g of fumaric acid is added to the evaporation residue in 25 ml of methanol. The mixture is stirred until a clear solution has formed and is then concentrated by evaporation. The residue is crystallised from 100 ml of acetonitrile/ethanol=95:5. The crystals are filtered off with suction and dried at 60° C. The title compound is obtained in the form of a white powder having a melting point of 95°-104° C.