Hydrochloric Acid → 6-(2,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-6-yl)hexanoic acid

HRID 517880Notes

Reaction equation

HRID 517880 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[N:33](C(OC(C)(C)C)=O)[C:14]2=[N:15][C:16]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[N:18]=[C:13]2[CH2:12][CH2:11]1)C.[OH-].[Na+].CO.Cl>CCO.O>[C:22]1([CH3:25])[CH:21]=[CH:20][C:19]([C:17]2[N:18]=[C:13]3[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:41])=[O:3])[NH:33][C:14]3=[N:15][C:16]=2[C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 89690447Tert-butyl 6-(6-ethoxy-6-oxohexyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Product 1

HCID 716574226-(2,3-Di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazin-6-yl)hexanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Tert-butyl 6-(6-ethoxy-6-oxohexyl)-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 4) (83 mg, 0.149 mmol) in EtOH (2 ml) was treated with 2M NaOH (0.223 ml, 0.446 mmol) and stirred at RT for 16 hours. MeOH (1 ml) and 2M HCl (0.372 ml, 0.744 mmol) were added and stirring continued at RT for 16 hours. The solvent was removed under reduced pressure and the residue was dissolved in water (30 ml). The mixture was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure. The crude product was dissolved in EtOH (1 ml) and treated with 2M NaOH (0.223 ml, 0.446 mmol). After stirring at RT overnight, the mixture was diluted with water (30 ml) and the pH was adjusted to pH1 using 1 M HCl. The aqueous portion was extracted with DCM (×3) and the combined organic extracts were concentrated under reduced pressure to afford an enantiomeric mixture.

Workup

  1. stirringstirring
  2. waitcontinued at RT for 16 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in water (30 ml)
  5. extractionThe mixture was extracted with DCM (×3)
  6. concentrationthe combined organic extracts were concentrated under reduced pressure
  7. dissolutionThe crude product was dissolved in EtOH (1 ml)
  8. stirringAfter stirring at RT overnight
  9. extractionThe aqueous portion was extracted with DCM (×3)
  10. concentrationthe combined organic extracts were concentrated under reduced pressure
  11. customto afford an enantiomeric mixture

Sources & evidence

ORD record
ord-ecdfc944bf5c4f659b526ec669676546
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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