Hydrochloric Acid → 7-(7-hydroxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 2276579Notes

Reaction equation

HRID 2276579 reaction equation
[OH:1][CH:2]1[CH2:25][N:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=[C:4]2[CH2:3]1.[OH-].[Na+].Cl>C(O)C>[OH:1][CH:2]1[CH2:25][N:24]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)[N:9]=[C:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 66665937ethyl 7-(7-hydroxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 666663317-(7-hydroxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Enantiomer 2 of ethyl 7-(7-hydroxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 3) (5.6 mg, 0.011 mmol) was dissolved in ethanol (0.5 ml) and 2M NaOH (0.023 ml, 0.046 mmol) was added. The solution was stirred at room temperature overnight under an atmosphere of nitrogen. 2M NaOH (0.023 ml, 0.046 mmol) was added to the mixture and the reaction was left to stir for a further hour at room temperature under an atmosphere of nitrogen. To the reaction mixture was added 2M HCl until the pH was below pH5. The volatile solvent was removed by distillation. To the residue was added water (10 ml) and the mixture was extracted with ethyl acetate (3×10 ml). The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as an oil which was dried in a vacuum oven at 40° C. overnight;

Workup

  1. waitthe reaction was left
  2. stirringto stir for a further hour at room temperature under an atmosphere of nitrogen
  3. customThe volatile solvent was removed by distillation
  4. additionTo the residue was added water (10 ml)
  5. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8d19aaf8da842268faa714f9b7e52af
Source dataset
uspto-grants-2015_09
Patent number
US09132127B2

Reaction notes

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