Hydrochloric Acid → HCID 11209508, compound

HRID 505444Notes

Reaction equation

HRID 505444 reaction equation
[C:1]([C:9]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:10]=1[C:11]([N:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:14])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl>CO.O1CCOCC1>[CH3:25][O:24][C:21]1[CH:20]=[C:10]2[C:9]([C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:15]([C:16]([O:18][CH3:19])=[O:17])[N:13]([CH3:14])[C:11]2=[O:12])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 58758882HCID 58758882, compound

Product 1

HCID 11209508HCID 11209508, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The amide 4 from the previous step was dissolved in methanol (10 ml) and treated with 25% NaOMe in methanol (1 ml). The resulting yellow mixture was then heated at 65 C for 1 h. After cooling to room temperature the reaction mixture was acidified with 1M HCl in dioxane. The resulting mixture was filtered to remove NaCl. The filtrate was concentrated and the residue purified by automated flash chromatography.

Workup

  1. temperatureThe resulting yellow mixture was then heated at 65 C for 1 h
  2. filtrationThe resulting mixture was filtered
  3. customto remove NaCl
  4. concentrationThe filtrate was concentrated
  5. customthe residue purified by automated flash chromatography

Sources & evidence

ORD record
ord-3e188346c33b49c780ecc5f44f5f2f3e
Source dataset
uspto-grants-2010_08
Patent number
US07781457B2

Reaction notes

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