Sodium Hydroxide → HCID 58135090, compound

HRID 1893533Notes

Reaction equation

HRID 1893533 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][N:6]([CH2:17][C:18]([O:20]CC)=[O:19])[C:7]1[CH:12]=[C:11]([C:13]([NH2:15])=O)[CH:10]=[CH:9][C:8]=1[CH3:16])C.[OH-].[Na+]>CO.O1CCCC1>[C:13]([C:11]1[CH:10]=[CH:9][C:8]([CH3:16])=[C:7]([N:6]([CH2:17][C:18]([OH:20])=[O:19])[CH2:5][C:4]([OH:23])=[O:3])[CH:12]=1)#[N:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66880540HCID 66880540, compound

Product 1

HCID 58135090HCID 58135090, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The compound (6.02 g, 19.8 mmol) obtained in step F was dissolved in a methanol-tetrahydrofuran=1:1 mixed solvent (100 ml). 1N sodium hydroxide (100 ml) was added with stirring at room temperature, and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid (110 ml) was added, and the aqueous layer was extracted 4 times with chloroform. The organic layer was mixed, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure, and the obtained solid was washed with diethyl ether-hexane mixed solvent, and dried under reduced pressure to give the title compound (4.26 g, yield 87%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid (110 ml)
  3. additionwas added
  4. extractionthe aqueous layer was extracted 4 times with chloroform
  5. additionThe organic layer was mixed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure
  9. washthe obtained solid was washed with diethyl ether-hexane mixed solvent
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-8d4879e3e6db417480da4539a555f441
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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