HCID 14787662, compound → HCID 14787663, compound

HRID 580415Notes

Reaction equation

HRID 580415 reaction equation
[CH3:1][C:2]([CH:11]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-])=O)([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4]>FC(F)(F)C(O)=O.[Pd].C(OCC)(=O)C>[CH3:1][C:2]([CH:11]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 1

HCID 14787662HCID 14787662, compound

Product 1

HCID 14787663HCID 14787663, compoundYield 95.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of α-methyl-[2-(2-nitrophenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (2.47 g, 6.38 mmol) in 24 ml of trifluoroacetic acid was catalytically hydrogenated (42 psi, 0.25 g of 10% palladium on charcoal) for 11/2 hours. The reaction suspension was filtered through a pad of Celite and concentrated in vacuo to yield a viscous brown oil. The crude product was dissolved in ethyl acetate and washed several times with saturated aqueous potassium carbonate solution. Evaporation of the ethyl acetate layer in vacuo yielded 2.27 g of a light tan solid. Recrystallization from methanol (3 crops) yielded 1.82 g of an off-white solid, melting point 165°-167° C.

Workup

  1. custom2 hours
  2. filtrationThe reaction suspension was filtered through a pad of Celite
  3. concentrationconcentrated in vacuo
  4. customto yield a viscous brown oil
  5. washwashed several times with saturated aqueous potassium carbonate solution
  6. customEvaporation of the ethyl acetate layer in vacuo

Sources & evidence

ORD record
ord-d1e4a84b90d744e996841aec0f701eb3
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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