(S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl ester → (S)-3-(4-Aminophenyl)-2-[3-(2-benzenesulfonylphenyl)ureido]propionic acid methyl ester

HRID 852244Notes

Reaction equation

HRID 852244 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])=[O:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1>C(O)C.[Ni]>[CH3:1][O:2][C:3](=[O:34])[C@@H:4]([NH:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:26])=[O:27])=[O:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 69377021(S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl ester

Product 1

HCID 69375729(S)-3-(4-Aminophenyl)-2-[3-(2-benzenesulfonylphenyl)ureido]propionic acid methyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-nitrophenyl) propionic acid methyl ester (3.64 g, 7.53 mmol) in ethanol (70 ml) was hydrogenated in the presence of a catalytic amount of Raney-Ni®. The catalyst was removed by filtration through Celite® and the solvent was eliminated under reduced pressure. The crude product was dissolved in dichloromethane (100 ml) and washed with saturated aqueous NaHCO3 (3×50 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield the title compound (3.1 g, 91%) as a yellow solid.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. dissolutionThe crude product was dissolved in dichloromethane (100 ml)
  3. washwashed with saturated aqueous NaHCO3 (3×50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99c4ea4963714f30b473fe2947a47a0e
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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