Hydrochloric Acid → HCID 67497105, compound

HRID 1628204Notes

Reaction equation

HRID 1628204 reaction equation
[O:1]=[C:2]([NH:19][C:20]1[N:21]=[C:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[S:23][CH:24]=1)[C@@H:3]([NH:11]C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[NH2:11][C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:2]([NH:19][C:20]1[N:21]=[C:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[S:23][CH:24]=1)=[O:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69620697HCID 69620697, compound

Product 1

HCID 67497105HCID 67497105, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a rt solution of 4.B (163 mg, 384 μmol) in dioxane (2.5 mL) was added 6.0 N HCl (1 mL). After stirring at rt for 30 min, the reaction mixture was poured into saturated aqueous NaHCO3 (5 m L), diluted with water (5 mL) and extracted by 30% iPrOH/CHCl3 (3×10 mL). The combined solution was washed with brine and dried over MgSO4. After removal of organic solvent under reduced pressure, purification of the residue by flash chromatography on silica gel using 0-20% MeOH/CH2Cl2 for elution provided 4.C as a colorless solid (105 mg, 85%)

Workup

  1. extractionextracted by 30% iPrOH/CHCl3 (3×10 mL)
  2. washThe combined solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter removal of organic solvent
  5. customunder reduced pressure, purification of the residue by flash chromatography on silica gel using 0-20% MeOH/CH2Cl2
  6. washfor elution

Sources & evidence

ORD record
ord-8a439034a03349bcab7b7bb3d210e04f
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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