Ethylacetate methanol → 3-(4-Methoxyanilino)-3-oxopropanoic acid

HRID 1629763Notes

Reaction equation

HRID 1629763 reaction equation
CN[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]([O:14]CC2C=CC=CC=2)=[O:13])=[CH:5][CH:4]=1.[H][H].C[CH2:26][O:27]C(C)=O.CO>[Pd]>[CH3:26][O:27][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 21584119Ethylacetate methanolHCID 86685854Benzyl 3-(4-(methylamino)phenylamino)-3-oxopropanoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 116585393-(4-Methoxyanilino)-3-oxopropanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst3×

Procedure

To a solution of Intermediate 6A (14.4 g, 4.8 mmol) in 10:1 EtOAc/MeOH (220 mL) was added 10% Pd/C (250 mg). The reaction mixture was stirred vigorously under an atmosphere of hydrogen (40 psi) for 2 h. More 10% Pd/C (250 mg) was added and the reaction was stirred under 50 psi hydrogen for another 1 h. Additional 10% Pd/C (500 mg) was added and the reaction was stirred under 50 psi hydrogen for an additional 1 h. The reaction was filtered through a pad of Celite® and the filtrate was concentrated in vacuo to yield Intermediate 6B (11.1 g, 96%) as an off-white solid. LCMS Anal. Calc'd for C10H11NO4 209.20, found [M+H] 210.1.

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d48835217c924a3abb5d498a45941731
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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