HCID 57584081, compound → HCID 57584031, compound

HRID 910616Notes

Reaction equation

HRID 910616 reaction equation
C([O:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18](=[O:36])[N:19]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]3)[CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)=[O:10])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH2:34]([O:33][C:31]([CH:28]1[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][N:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([C:9]([OH:10])=[O:8])=[CH:16][CH:15]=3)[C:18]2=[O:36])[CH2:30][CH2:29]1)=[O:32])[CH3:35]

Participants

5

Reactant 2

HCID 57584081HCID 57584081, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57584031HCID 57584031, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd—C (360 mg) was added to an ethanol (30 ml) solution of ethyl 1-{2-[3-{4-[(benzyloxy)carbonyl]phenyl}-2-oxopyridin-1(2H)-yl]ethyl}piperidin-4-carboxylate (1.647 g), followed by stirring in a hydrogen atmosphere under normal pressure at room temperature for 27 hours. The reaction mixture was filtered through Celite, washed with THF and ethanol, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 80:20) to obtain 4-(1-{2-[4-(ethoxycarbonyl)piperidin-1-yl]ethyl}-2-oxo-1,2-dihydropyridin-3-yl)benzoic acid (671 mg) as a pale yellow amorphous solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with THF and ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 80:20)

Sources & evidence

ORD record
ord-4257a6288107498ca1b6dd4ab69fe87e
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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