Sodium Hydroxide → HCID 66899191, compound

HRID 877263Notes

Reaction equation

HRID 877263 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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 58136341HCID 58136341, compound

Product 1

HCID 66899191HCID 66899191, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

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.

Workup

  1. extractionthe mixture was extracted repeatedly with dichloromethane
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-3d08f8c568604e47b03c8c55016f5864
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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