Hydrochloric Acid → HCID 59389274, compound

HRID 2357933Notes

Reaction equation

HRID 2357933 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]2[C:16]3[N:17]([N:23]=[C:24]([CH:30]([CH3:32])[CH3:31])[C:25]=3[C:26]([O:28]C)=[O:27])[C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1.O.CO>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]2[C:16]3[N:17]([N:23]=[C:24]([CH:30]([CH3:32])[CH3:31])[C:25]=3[C:26]([OH:28])=[O:27])[C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59389342HCID 59389342, compound

Product 1

HCID 59389274HCID 59389274, compoundYield 49.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of Example 266 (250 mg) and lithium hydroxide (140 mg) in a mixture of THF, water and methanol (6 mL, THF:water:methanol=3:2:1) was refluxed for 18 hours. Subsequently, water was added, followed by addition of 2 mol/L hydrochloric acid to adjust the pH to 4. The mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=98:2) to afford the title compound as a colorless powder (120 mg).

Workup

  1. temperaturewas refluxed for 18 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solvent was concentrated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=98:2)

Sources & evidence

ORD record
ord-258009b23092401d82d47faa38c425f3
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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