Hydrochloric Acid → HCID 58135287, compound

HRID 1893540Notes

Reaction equation

HRID 1893540 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][N:6]([CH2:19][C:20]([O:22]CC)=[O:21])[C:7]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:9][C:8]=1[CH3:18])C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[CH2:16]([O:15][C:13]([C:11]1[CH:10]=[CH:9][C:8]([CH3:18])=[C:7]([N:6]([CH2:5][C:4]([OH:25])=[O:3])[CH2:19][C:20]([OH:22])=[O:21])[CH:12]=1)=[O:14])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66880995HCID 66880995, compound

Product 1

HCID 58135287HCID 58135287, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (0.62 g, 1.76 mmol) obtained in step A was dissolved in a ethanol (10 ml)-tetrahydrofuran (5 ml) mixed solvent, 1N sodium hydroxide (3.53 ml, 3.53 mmol) was added at room temperature with stirring, and the mixture was stirred at the same temperature for 90 min. To the reaction mixture was added 1N hydrochloric acid (5 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (0.52 g) as a crude colorless oil.

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at the same temperature for 90 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with diluted hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a72c64743365426d962559e226ce3840
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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