Hydrochloric Acid → HCID 11156490, compound

Reaction equation

C([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([S:20][C:21]3[N:25]([CH3:26])[C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[N:23][N:22]=3)=[CH:16][C:15]=2[O:34][CH2:35][CH2:36][CH3:37])=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH2:27]([C:24]1[N:25]([CH3:26])[C:21]([S:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][NH:12][C:9]3[CH:8]=[CH:7][C:6]([CH2:5][C:4]([OH:38])=[O:3])=[CH:11][CH:10]=3)=[C:15]([O:34][CH2:35][CH2:36][CH3:37])[CH:16]=2)=[N:22][N:23]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

Procedure

A solution of {4-[4-(5-heptyl-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl)-2-propoxybenzylamino]phenyl}acetic acid ethyl ester obtained in Example 31 (0.7 g, 2.39 mmol), 2M aqueous potassium carbonate (9 ml) in methanol (20 ml) is heated under reflux for 3 hours. The reaction medium is acidified at room temperature with a 2N hydrochloric acid solution to pH 5. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate. After evaporation of the solvents, 0.592 g (89%) of the expected compound are recovered in the form of a yellow amorphous solid.