Sodium Hydroxide → rac-7-(7-Methoxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 406239Notes

Reaction equation

HRID 406239 reaction equation
[CH3:1][O:2][CH:3]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:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[N:10]=[C:5]2[CH2:4]1.[OH-].[Na+]>CO>[CH3:1][O:2][CH:3]1[CH2:26][N:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:6]2=[N:7][C:8]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)[N:10]=[C:5]2[CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 131731628rac-Ethyl 7-(7-methoxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 66666114rac-7-(7-Methoxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

rac-Ethyl 7-(7-methoxy-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1) (139 mg, 0.277 mmol) in MeOH (3 ml) at RT was treated with 2M NaOH (416 μL, 0.831 mmol) and the mixture was stirred at RT for 4 hours. A further portion of 2M NaOH (416 μL, 0.831 mmol) was added the reaction mixture was stirred at RT overnight. The organic solvent was removed in vacuo and the resulting aqueous portion was diluted with water (20 ml). The pH was adjusted to pH1 using 2M HCl and the mixture was extracted with DCM (×3). The combined organic extracts were isolated using a phase separating cartridge and the solvent was removed in vacuo. Purification of the crude product by chromatography on silica eluting with 0-30% EtOAc/iso-hexane followed by 10% MeOH in EtOAc afforded the title compound;

Workup

  1. stirringwas stirred at RT overnight
  2. customThe organic solvent was removed in vacuo
  3. additionthe resulting aqueous portion was diluted with water (20 ml)
  4. extractionthe mixture was extracted with DCM (×3)
  5. customThe combined organic extracts were isolated
  6. customseparating cartridge
  7. customthe solvent was removed in vacuo
  8. customPurification of the crude product by chromatography on silica eluting with 0-30% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-c68778a51ee54fbc954a73986c94bf2f
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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