Hydrochloric Acid → HCID 59218427, compound

HRID 2246680Notes

Reaction equation

HRID 2246680 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([CH3:35])[C:13]2[N:12]=[C:11]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]([C:29]4[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=4)[CH2:23][C:24]([O:26]CC)=[O:25])=[CH:18][CH:17]=3)[CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1.Cl>CCO>[CH3:3][C:4]1([CH3:35])[C:13]2[N:12]=[C:11]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]([C:29]4[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=4)[CH2:23][C:24]([OH:26])=[O:25])=[CH:18][CH:17]=3)[CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59218507HCID 59218507, compound

Product 1

HCID 59218427HCID 59218427, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10% NaOH (aq) (1 mL) is added to a solution of compound 54.1 (45 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 the compound 54.

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-dee628dc834e462282140c018ef88caa
Source dataset
uspto-grants-2010_03
Patent number
US07687526B2

Reaction notes

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