Hydrochloric Acid → HCID 66933216, compound

HRID 877275Notes

Reaction equation

HRID 877275 reaction equation
[CH:1]1([CH:6]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]3[C:35](=[O:36])[CH2:34][O:33][C:32]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[N:31]3)=[CH:25][CH:24]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12](/[CH:16]=[CH:17]/[C:18]([O:20]CC)=[O:19])[CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCOCC1.O>[CH:1]1([CH:6]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]3[C:35](=[O:36])[CH2:34][O:33][C:32]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[N:31]3)=[CH:25][CH:24]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][C:18]([OH:20])=[O:19])[CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58136774HCID 58136774, compound

Product 1

HCID 66933216HCID 66933216, compound

Reagents, catalysts & solvents 1

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

Procedure

827 mg (1.461 mmol) of ethyl (2E)-3-{3-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]phenyl}prop-2-enoate (Example 174A) were dissolved in 28 ml of dioxane/water (3:1 v/v), and 2.2 ml of 1 N aqueous sodium hydroxide solution were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then acidified to pH 1 with 1 N hydrochloric acid and extracted repeatedly with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. This gave 780 mg (95% of theory) of the target compound.

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9767b42142d6484fa77dde46f084be29
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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