Lithium hydroxide, monohydrate → HCID 58136703, compound

HRID 877161Notes

Reaction equation

HRID 877161 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH2:13][C:14](=[O:34])[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]([CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[C:25]([O:27]C)=[O:26])=[CH:20][CH:19]=3)[N:16]=2)=[CH:7][CH:6]=1>O1CCOCC1.O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH2:13][C:14](=[O:34])[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]([CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[C:25]([OH:27])=[O:26])=[CH:20][CH:19]=3)[N:16]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58136649HCID 58136649, compound

Product 1

HCID 58136703HCID 58136703, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

86 mg (2.04 mmol) of lithium hydroxide monohydrate were added to a solution of 450 mg (1.02 mmol) of methyl (4-{[2-(4-chlorophenyl)-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl]methyl}phenyl)(cyclopentyl)acetate in 10 ml of dioxane and 10 ml of water, and the mixture was stirred at 80° C. for 12 h. After removal of the dioxane under reduced pressure, the aqueous phase was adjusted to pH 2 using 1 M hydrochloric acid, which resulted in the flocculation of the product. The solution was filtered and the filter residue was dried under reduced pressure. This gave 373 mg (0.87 mmol, 86% of theory) of the title compound as a white solid.

Workup

  1. customAfter removal of the dioxane under reduced pressure
  2. customresulted in the flocculation of the product
  3. filtrationThe solution was filtered
  4. customthe filter residue was dried under reduced pressure

Sources & evidence

ORD record
ord-8e1f0bc0762640dc85851b9e7dc097ec
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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