HCID 19698358, compound → HCID 19698379, compound

HRID 1439897Notes

Reaction equation

HRID 1439897 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:21]([O-])=O)=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH2:21])=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 19698358HCID 19698358, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19698379HCID 19698379, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 5-tert-butoxycarbonylaminomethyl-2-nitrophenylacetate (6.8 g, 21 mmol) in methanol (250 mL) in the presence of 10% Pd/C was hydrogenated under atmospheric pressure of hydrogen at room temperature. The catalyst was removed by filtration through celite and the filtrate was concentrated to give 5.8 g of the title compound: 1H NMR (CDCl3) δ 7.02 (d, 1H, J=7.6 Hz), 7.00 (s, 1H), 6.67 (d, 1H, J=7.6 Hz), 4.72 (br, 1H), 4.18 (d, 2H, J=5.7 Hz), 4.05 (br, 2H), 3.55 (s, 2H), 1.46 (s, 9H).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0311306e3d554d4d87bd6de7652344a1
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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