Hydrochloric Acid → HCID 66977532, compound

HRID 1041912Notes

Reaction equation

HRID 1041912 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=3)[CH:18]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+].C(=O)(O)[O-].[Na+].Cl>CO>[CH:22]([C:19]1[N:17]2[CH:18]=[C:13]([O:12][CH:9]3[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:25])=[O:3])[CH2:7][CH2:8]3)[CH:14]=[CH:15][C:16]2=[N:21][N:20]=1)([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 66977570HCID 66977570, compound

Product 1

HCID 66977532HCID 66977532, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 22 step a (50 mg, 0.145 mmol) and 1N sodium hydroxide (0.5 mL, 0.5 mmol) in MeOH (2 mL) was stirred at RT for 16 h. The reaction mixture was treated with sat. aq. sodium bicarbonate, evaporated to dryness, and purified on a reverse phase FCC (water/MeOH 100/0.0 to 0/100) to give two fractions. The first eluting fraction was acidified to pH 5 with 1N HCl solution and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, combined with the second eluting fraction from chromatography and concentrated in vacuo. The resulting residue was dissolved in MeOH/EtOAc (1:1, 10 mL), filtered and evaporated to dryness to give the title compound as a pale brown solid (27 mg, 59%). LCMS (Method 5): Rt 3.58-3.65 min, m/z 318 [MH+].

Workup

  1. customevaporated to dryness
  2. custompurified on a reverse phase FCC (water/MeOH 100/0.0 to 0/100)
  3. customto give two fractions
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting residue was dissolved in MeOH/EtOAc (1:1, 10 mL)
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-c9c302aa8d0e4bb698f374b2522db657
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

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