Hydrochloric Acid → HCID 86611785, compound

HRID 732858Notes

Reaction equation

HRID 732858 reaction equation
C([O:8][C:9](=[O:26])[CH:10]([O:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C1C=CC=CC=1.[OH-].[Na+].Cl>CO>[C:19]([NH:18][O:17][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:9]([OH:26])=[O:8])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86611784HCID 86611784, compound

Product 1

HCID 86611785HCID 86611785, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the compound from Step 4c (2.8 g, 7.8 mmol) and 1 N NaOH (15 mL, 15 mmol) in MeOH (30 mL) was stirred at room temperature for 3 hours. The reaction mixture was neutralized by 2 N HCl to pH ˜2. The resulting mixture was extracted with EtOAc (50 mL×3). The combined organic phases were washed with NH4Cl and brine, dried (Na2SO4) and filtered. The filtrate was concentrated and residue was purified by flash chromatography (silica gel, EtOAc/CH2Cl2=1/4) giving 0.6 g (29%) of the title compound.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (50 mL×3)
  2. washThe combined organic phases were washed with NH4Cl and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customresidue was purified by flash chromatography (silica gel, EtOAc/CH2Cl2=1/4)

Sources & evidence

ORD record
ord-e4c57e9f0afe42b2bbe44ec45295be2c
Source dataset
uspto-grants-2009_09
Patent number
US07589067B2

Reaction notes

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