Sodium Hydroxide → HCID 67435012, compound

HRID 1946504Notes

Reaction equation

HRID 1946504 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[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[NH3:9].[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[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58460146HCID 58460146, compound

Product 1

HCID 67435012HCID 67435012, compoundYield 174.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate 35 (496 mg) was dissolved in ethanol (5 ml) and the resulting soln. was treated with sodium hydroxide, 2M aq (3 ml). The resulting suspension was heated to reflux for 4 hr. 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 1 hr. Reaction mixture concentrated in vacuo. The residue was purified by reverse phase chromatography using acetonitrile water with an ammonium carbonate modifier gradient. The desired fractions were combined and concentrated under vacuum to give the title compound (304 mg) as a white solid. LC/MS MH+ 347, Rt 1.93 min (5 minute run).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 4 hr
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. temperatureheated
  6. temperatureto reflux for 1 hr
  7. customReaction mixture
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by reverse phase chromatography
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9cca8a342ae4444bb876a7c9235f8a40
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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