3-Benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine → 3-(2-Cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl) pyridine-5-carboxylic acid

HRID 396671Notes

Reaction equation

HRID 396671 reaction equation
C([O:8][C:9]([C:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:15]([C:26]([O:28][CH2:29][CH2:30][C:31]#[N:32])=[O:27])=[C:14]([CH3:33])[NH:13][C:12]=1[CH3:34])=[O:10])C1C=CC=CC=1.C(O)=O.CO>C(Cl)(Cl)Cl.[Pd]>[C:31]([CH2:30][CH2:29][O:28][C:26]([C:15]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[C:11]([C:9]([OH:10])=[O:8])=[C:12]([CH3:34])[NH:13][C:14]=1[CH3:33])=[O:27])#[N:32]

Participants

5

Reactant 2

HCID 107188283-Benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridineHCID 18963719Formic acid methanol

Product 1

HCID 104994373-(2-Cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl) pyridine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 3-benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine (3.24 g, 7.02 mmol) in 160 ml of 4.4%(w/w) formic acid/MeOH mixture was stirred with Pd/C (10%, 3.24 g) for 30 min., the reaction was quenched by addition of 10 ml of CHCl3. The mixture was filtered and concentrated to give a yellow powder, which was dissolved in CHCl3 (100 ml), washed with water (25 ml) and aqueous 1N HCl (25 ml). After drying (Na2SO4) and evaporation of solvent, 3-(2-cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl) pyridine-5-carboxylic acid was obtained as a yellow powder (1.94 g, 75%).

Workup

  1. customthe reaction was quenched by addition of 10 ml of CHCl3
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customto give a yellow powder, which
  5. washwashed with water (25 ml) and aqueous 1N HCl (25 ml)
  6. customAfter drying
  7. custom(Na2SO4) and evaporation of solvent

Sources & evidence

ORD record
ord-bb5aba4b99494601b3e0548b198105fd
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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