Sodium Hydroxide → HCID 44513413, compound

HRID 877278Notes

Reaction equation

HRID 877278 reaction equation
[OH-].[Na+].[CH:3]1([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]3[C:36](=[O:37])[CH2:35][O:34][C:33]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[N:32]3)=[CH:26][CH:25]=2)[C:9]([NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21]CC)=[O:20])[CH2:15][CH2:14]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1>O1CCOCC1>[CH:3]1([CH:8]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][N:31]3[C:36](=[O:37])[CH2:35][O:34][C:33]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[N:32]3)=[CH:28][CH:29]=2)[C:9]([NH:11][CH2:12][CH:13]2[CH2:14][CH2:15][CH:16]([C:19]([OH:21])=[O:20])[CH2:17][CH2:18]2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58136351HCID 58136351, compound

Product 1

HCID 44513413HCID 44513413, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.55 ml (1.11 mmol) of 2 M aqueous sodium hydroxide solution was added to a solution of 31 mg (55 μmol) of ethyl 4-{[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]methyl}cyclohexanecarboxylate (Example 127A) in 3 ml of dioxane, and the mixture was stirred at room temperature overnight. The reaction mixture was then extracted once with tert-butyl methyl ether. The aqueous phase was then adjusted to pH 2 with 1 M hydrochloric acid and extracted twice with ethyl acetate. The ethyl acetate phases were combined and dried over sodium sulfate. After filtration, the solvent was removed to dryness. This gave 25 mg (47 μmol, 85% of theory) of the title compound as a colorless solid.

Workup

  1. extractionThe reaction mixture was then extracted once with tert-butyl methyl ether
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was removed to dryness

Sources & evidence

ORD record
ord-a4640485c8094ae5ad754a0fdecb353d
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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