Sodium Hydroxide → HCID 58074531, compound

HRID 238182Notes

Reaction equation

HRID 238182 reaction equation
[OH-].[Na+].[F:3][C:4]([F:34])([F:33])[CH:5]([CH3:32])[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:24](=[O:25])[CH2:23][O:22][C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:20]2)=[CH:14][CH:13]=1)[C:7]([O:9]CC)=[O:8]>O1CCOCC1>[F:34][C:4]([F:3])([F:33])[CH:5]([CH3:32])[CH:6]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][N:19]2[C:24](=[O:25])[CH2:23][O:22][C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:20]2)=[CH:16][CH:17]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58074496HCID 58074496, compound

Product 1

HCID 58074531HCID 58074531, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

11.4 ml (11.4 mmol) of 1 N aqueous sodium hydroxide solution were added to a solution of 1283 mg (2.86 mmol) of ethyl 4,4,4-trifluoro-3-methyl-2-{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}butanoate in 10 ml of dioxane, and the mixture was stirred at 80° C. overnight. After the reaction had gone to completion, the dioxane was removed under reduced pressure and the solution that remained was diluted with water and then adjusted to pH 2 with 1 M hydrochloric acid. The precipitated solid was filtered off, washed with water and dried under reduced pressure at 45° C. overnight. This gave 1058 mg (2.52 mmol, 88% of theory) of the title compound as an isomer mixture.

Workup

  1. customthe dioxane was removed under reduced pressure
  2. additionthe solution that remained was diluted with water
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customdried under reduced pressure at 45° C. overnight

Sources & evidence

ORD record
ord-fa370529221d44a6aa88aa60b45fb7e8
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Reaction notes

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