Hydrochloric Acid → HCID 59389365, compound

HRID 2357916Notes

Reaction equation

HRID 2357916 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:23]=[C:8]2[C:9]([C:15](=[O:22])[CH:16](C)[C:17](OC)=O)=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[N:7]2[N:6]=1)[CH3:4].Cl>CO>[CH2:3]([C:5]1[CH:23]=[C:8]2[C:9]([C:15](=[O:22])[CH2:16][CH3:17])=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[N:7]2[N:6]=1)[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59389322HCID 59389322, compound

Product 1

HCID 59389365HCID 59389365, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 mol/L aqueous sodium hydroxide solution (12 mL) was added to a solution of the compound of Example 184 (460 mg) in methanol (30 mL). The mixture was stirred at room temperature for 2 days. Subsequently, diluted hydrochloric acid was added to make the mixture acidic. Methanol was evaporated and the residue was extracted with ethyl acetate (×2). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=2:3) afforded the title compound as a pale green powder (295 mg).

Workup

  1. customMethanol was evaporated
  2. extractionthe residue was extracted with ethyl acetate (×2)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-247ada88797a4605bcad6be4b2afc7c5
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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