Hydrochloric Acid → rac-7-(7,8-Dihydroxy-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 406198Notes

Reaction equation

HRID 406198 reaction equation
C([O:4][CH:5]1[CH2:26][N:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])[C:8]2=[N:9][C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=[C:7]2[CH:6]1[O:38]C(=O)C)(=O)C.[Li+].[OH-].Cl>C1COCC1.O>[OH:4][CH:5]1[CH2:26][N:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:8]2=[N:9][C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:12]=[C:7]2[CH:6]1[OH:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 123258647rac-5-(7-Ethoxy-7-oxoheptyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine-7,8-diyl diacetate

Product 1

HCID 56644910rac-7-(7,8-Dihydroxy-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of rac-5-(7-ethoxy-7-oxoheptyl)-2,3-diphenyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine-7,8-diyl diacetate (step 1) (30 mg, 0.054 mmol) in THF (3 ml) and water (1.0 ml) was added LiOH (7.70 mg, 0.322 mmol). The suspension was heated to reflux for 1 hour and allowed to stand at RT overnight. The mixture was again heated at reflux for 30 minutes and after cooling to RT, 1M HCl was added to adjust the pH to below pH 5. The volatile solvent was evaporated and the resulting mixture was extracted with EtOAc (10 ml). The organic extract was washed with water, dried over MgSO4, filtered and concentrated in vacuo to afford a mixture of the title products;

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was again heated
  4. temperatureat reflux for 30 minutes
  5. customThe volatile solvent was evaporated
  6. extractionthe resulting mixture was extracted with EtOAc (10 ml)
  7. extractionThe organic extract
  8. washwas washed with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford

Sources & evidence

ORD record
ord-f02dffde37974e44b21bbfa59ba40105
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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