HCID 86611789, compound → HCID 86611788, compound

HRID 732864Notes

Reaction equation

HRID 732864 reaction equation
C([O:3][C:4](=[O:23])[CH:5]([O:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C>CO.[OH-].[Na+]>[C:16]([NH:15][O:14][CH:5]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([OH:23])=[O:3])([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17]

Participants

4

Reactant 1

HCID 86611789HCID 86611789, compound

Product 1

HCID 86611788HCID 86611788, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of the compound from Step 9b (950 mg, 3 mmol) in MeOH (20 mL) and 2 N NaOH (4 mL) were stirred at room temperature for 3 hours. The mixture was concentrated under reduced pressure, acidified to pH ˜2.0 with 2 N HCl. The resulting mixture was extracted with EtOAc (3×50 mL), dried (Na2SO4) and filtered. The solvent was removed under reduced pressure and residue was purified by flash chromatography (CH2Cl2; CH2Cl2/MeOH=10/1) giving 900 mg (86%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionThe resulting mixture was extracted with EtOAc (3×50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure and residue
  6. customwas purified by flash chromatography (CH2Cl2; CH2Cl2/MeOH=10/1)

Sources & evidence

ORD record
ord-58d402b1c622430786c9510a163fcc37
Source dataset
uspto-grants-2009_09
Patent number
US07589067B2

Reaction notes

Loading…