HCID 18360792, compound → HCID 23004164, compound

HRID 382738Notes

Reaction equation

HRID 382738 reaction equation
C([O:8][C:9]([C:11]1[CH:12]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)[C:13]([C:23]([O:25][CH2:26][CH2:27][C:28]#[N:29])=[O:24])=[C:14]([CH2:20][CH2:21][CH3:22])[NH:15][C:16]=1[CH2:17][CH2:18][CH3:19])=[O:10])C1C=CC=CC=1.C(O)=O.CO>C(Cl)(Cl)Cl.[Pd]>[C:28]([CH2:27][CH2:26][O:25][C:23]([C:13]1[CH:12]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)[C:11]([C:9]([OH:10])=[O:8])=[C:16]([CH2:17][CH2:18][CH3:19])[NH:15][C:14]=1[CH2:20][CH2:21][CH3:22])=[O:24])#[N:29]

Participants

5

Reactant 2

HCID 18360792HCID 18360792, compoundHCID 18963719Formic acid methanol

Product 1

HCID 23004164HCID 23004164, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 5-benzyloxycarbonyl-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-4-(4-nitrophenyl)-2,6-dipropylpyridine (10.6 g, 20.4 mmol) in 200 ml of 4.4% (w/w) formic acid/MeOH mixture was stirred with Pd/C (10%, 3.50 g) at room temperature. After 1 hr, the reaction was quenched by addition of 50 ml of CHCl3. The mixture was filtered and concentrated to give a yellow powder, which was dissolved in CHCl3 (250 ml), washed with 0.5N aqueous HCl (100 ml) and brine (100 ml), then dried, over Na2SO4. After filtration and evaporation of solvent, 3-(2-cyanoethoxy)carbonyl-1,4-dihydro-4-(4-nitrophenyl)-2,6-dipropylpyridine-5-carboxylic acid was obtained as a yellow powder (8.04 g, 92%).

Workup

  1. customthe reaction was quenched by addition of 50 ml of CHCl3
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. customto give a yellow powder, which
  5. washwashed with 0.5N aqueous HCl (100 ml) and brine (100 ml)
  6. dry with materialdried, over Na2SO4
  7. filtrationAfter filtration and evaporation of solvent

Sources & evidence

ORD record
ord-b99d8dcb4d7547caaa196a51aed3e3f5
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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