Hydrochloric Acid → HCID 59218452, compound

HRID 2246681Notes

Reaction equation

HRID 2246681 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C@H:9]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:33]=[N:32][C:31]3[C:30]([CH3:35])([CH3:34])[CH2:29][CH2:28][C:27]([CH3:37])([CH3:36])[C:26]=3[N:25]=2)=[CH:18][CH:17]=1)[CH2:10][C:11]([O:13]CC)=[O:12].Cl>CCO>[CH3:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C@H:9]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]2[CH:33]=[N:32][C:31]3[C:30]([CH3:35])([CH3:34])[CH2:29][CH2:28][C:27]([CH3:37])([CH3:36])[C:26]=3[N:25]=2)=[CH:20][CH:21]=1)[CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59218460HCID 59218460, compound

Product 1

HCID 59218452HCID 59218452, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10% NaOH(aq) (1 mL) is added to a solution of compound 55 (47 mg, 0.1 mmol) in EtOH (2 mL). The reaction mixture is stirred at room temperature for 4 hours. 1N HCl is added to neutralize the mixture to pH 6-7. The mixture is extracted with EtOAc (2×20 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is flash chromatographed (silica gel, 0-10% MeOH in DCM) to afford compound 56.

Workup

  1. extractionThe mixture is extracted with EtOAc (2×20 mL)
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed (silica gel, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-a087e2ad764848ab88dbba738e483af2
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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