Sodium Hydroxide → HCID 66899191, compound

Reaction equation

[CH:1]1([CH:6]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:33](=[O:34])[CH2:32][O:31][C:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[N:29]3)=[CH:23][CH:22]=2)[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19]C)=[O:18])=[CH:13][CH:12]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[Cl-].[NH4+]>O1CCOCC1.O>[CH:1]1([CH:6]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[C:33](=[O:34])[CH2:32][O:31][C:30]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[N:29]3)=[CH:23][CH:22]=2)[C:7]([NH:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[CH:15][CH:16]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Procedure

969 mg (1.757 mmol) of methyl 4-{[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]methyl}benzenecarboxylate (Example 113A) were dissolved in 30 ml of dioxane/water (3:1 v/v), and 3.87 ml (3.865 mmol) of 1 N aqueous sodium hydroxide solution were added. The mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was then added, and the mixture was extracted repeatedly with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. This gave 803 mg (1.53 mmol, 87% of theory) of the title compound.