Sodium Hydroxide → HCID 46829880, compound

HRID 1946527Notes

Reaction equation

HRID 1946527 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([C:17](C(OCC)=O)(C(OCC)=O)[C:18]([O:20]CC)=[O:19])[CH2:15][CH2:16][C:12]=3[N:11]=[C:10]2[CH:33]([CH3:35])[CH3:34])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][CH2:16][C:12]=3[N:11]=[C:10]2[CH:33]([CH3:35])[CH3:34])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58460151HCID 58460151, compound

Product 1

HCID 46829880HCID 46829880, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate 20 (250 mg) was dissolved in ethanol (10 ml) and the resulting soln was treated with sodium hydroxide, 3M aq (4 ml). The resulting suspension was heated to reflux for 4 h. The reaction mixture was allowed to cool and concentrated in vacuo. The crude residue was taken up in Acetic Acid (10.00 ml) and heated to reflux for 2 h. Reaction mixture concentrated in vacuo and was purified by Reverse Phase chromatography using a 5->80% gradient of Acetonitrile/water with an ammonium carbonate modifier over 12 column volumes. The desired fractions were combined and concentrated under vacuum to give material that was repurified by Reverse Phase chromatography using a 5->80% gradient of acetonitrile water with 0.1% formic acid. The desired fractions were combined and concentrated under vacuum to give the title compound (33 mg). MH+=333 LC/MS MH+333, Rt 1.84 min (5 min run).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 4 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. temperatureheated
  6. temperatureto reflux for 2 h
  7. customReaction mixture
  8. concentrationconcentrated in vacuo
  9. customwas purified by Reverse Phase chromatography
  10. concentrationconcentrated under vacuum
  11. customto give material that
  12. customwas repurified by Reverse Phase chromatography
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1b50486e4b9941fd9ea7474100e716d4
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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