Lithium hydroxide, monohydrate → 7-(7-Ethyl-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 517886Notes

Reaction equation

HRID 517886 reaction equation
[CH2:1]([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)[CH3:2].O[Li].O>C1COCC1.O>[CH2:1]([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:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=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)[CH3:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 89690091Ethyl 7-(7-ethyl-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 716574257-(7-Ethyl-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A (0° C.) cooled solution of ethyl 7-(7-ethyl-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (0.22 g, 0.44 mmol) in THF:H2O (4:1, 5 ml) was treated with LiOH.H2O (0.072 g, 1.76 mmol) and stirred at RT overnight. A further 2 equivalents of LiOH.H2O was added and the reaction mixture was heated to 50° C. for 4 hours. The solvent was removed under reduced pressure and the aqueous layer was acidified to pH 3 and partitioned between water and ethyl acetate. The organic layer was washed with saturated brine solution, dried over anhydrous sodium sulphate and concentrated under vacuum. The crude material was purified by chromatography on silica eluting with 10% EtOAc in hexane followed by preparative HPLC (MeCN in water eluent) to afford the titled compound;

Workup

  1. temperaturethe reaction mixture was heated to 50° C. for 4 hours
  2. customThe solvent was removed under reduced pressure
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe crude material was purified by chromatography on silica eluting with 10% EtOAc in hexane

Sources & evidence

ORD record
ord-9a1885ab865d443c991ad756ef80df7d
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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