Sodium Hydroxide → rac-7-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)-3-hydroxyheptanoic acid

HRID 517918Notes

Reaction equation

HRID 517918 reaction equation
[C:1]1([CH3:35])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([OH:34])[CH2:29][C:30]([O:32]C)=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.[OH-].[Na+]>CCO.O>[C:1]1([CH3:35])[CH:2]=[CH:3][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([OH:34])[CH2:29][C:30]([OH:32])=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89689978Methyl 7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)-3-hydroxyheptanoate

Product 1

HCID 78140344rac-7-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)-3-hydroxyheptanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)-3-hydroxy heptanoate (step 3)(43 mg, 0.091 mmol) in EtOH (908 μL) was treated with sodium hydroxide (136 μL, 0.272 mmol) and stirred at room temperature for 1 hour. The resulting mixture was diluted with water (2 ml) and acidified to pH 2. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried by passing through a phase separator and concentrated under reduced pressure to give an oil. The oil was purified by flash column chromatography using the ISCO combiflash Rf, eluting with 0-50% EtOAc (containing 10% MeOH) in iso-hexane on a 4 g silca cartridge. The product fractions were combined and the solvent removed under reduced pressure to yield the titled compound as a colourless oil;

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic extracts were washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. customThe oil was purified by flash column chromatography
  7. washeluting with 0-50% EtOAc (containing 10% MeOH) in iso-hexane on a 4 g silca cartridge
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-62a689a17fbb423089bd243be59730a6
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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