Hydrochloric Acid → HCID 58136712, compound

HRID 877277Notes

Reaction equation

HRID 877277 reaction equation
[OH-].[Na+].[CH:3]1([CH:8]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]3[C:37](=[O:38])[CH2:36][O:35][C:34]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[N:33]3)=[CH:27][CH:26]=2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[CH:15]=[CH:16][CH:17]=2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>O1CCOCC1.O>[CH:3]1([CH:8]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:32]3[C:37](=[O:38])[CH2:36][O:35][C:34]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)=[N:33]3)=[CH:27][CH:26]=2)[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:15]=[CH:16][CH:17]=2)=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58136565HCID 58136565, compound

Product 1

HCID 58136712HCID 58136712, compound

Reagents, catalysts & solvents 1

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

Procedure

11.05 ml of 1 N aqueous sodium hydroxide solution were added to a solution of 4.18 g (7.363 mmol) of ethyl 3-{3-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]phenyl}propanoate (Example 180A) in 195 ml of dioxane/water (4:1 v/v). The mixture was stirred at room temperature overnight and 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 on a rotary evaporator. The crude product was dissolved in ethyl acetate and filtered through silica gel. Activated carbon was added to the filtrate, and the mixture was heated at reflux and filtered through Tonsil. Concentration under reduced pressure gave 3.20 g (81% of theory) of the title 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 on a rotary evaporator
  5. dissolutionThe crude product was dissolved in ethyl acetate
  6. filtrationfiltered through silica gel
  7. additionActivated carbon was added to the filtrate
  8. temperaturethe mixture was heated
  9. temperatureat reflux
  10. filtrationfiltered through Tonsil
  11. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-85fe79741ca54325b50ca2f5180f2ff6
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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