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

HRID 406196Notes

Reaction equation

HRID 406196 reaction equation
[CH2:1]([CH:3]1[C:12]2[C:7](=[N:8][C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=2)[N:6]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:5][CH2:4]1)[CH3:2].[Li+].[OH-].Cl>C1COCC1.O>[CH2:1]([CH:3]1[C:12]2[C:7](=[N:8][C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:11]=2)[N:6]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 123432560rac-Ethyl 7-(8-ethyl-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 66665375rac-7-(8-Ethyl-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-ethyl 7-(8-ethyl-2,3-diphenyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1) (15 mg, 0.032 mmol) in THF (4.5 ml) and water (1.5 ml) was added LiOH (4.57 mg, 0.191 mmol). The reaction mixture was heated to reflux for 3.5 hours and stirred at RT overnight. The pH of the reaction mixture was adjusted to pH<5 by addition of 2M HCl. The volatile solvent was removed in vacuo and the crude residue was dissolved in water (10 ml) and extracted with EtOAc (3×10 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound;

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. customThe volatile solvent was removed in vacuo
  4. dissolutionthe crude residue was dissolved in water (10 ml)
  5. extractionextracted with EtOAc (3×10 ml)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a1ebeab4c18f49548e0f4e3b07354e98
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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