Stannous chloride dihydrate → N-(4-Amino-2-phenylbenzoyl)methionine methyl ester

HRID 1739138Notes

Reaction equation

HRID 1739138 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 18666764(4-Nitro-2-phenylbenzoyl)methionine methyl ester

Product 1

HCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl esterYield 74.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-nitro-2-phenylbenzoyl methionine methyl ester (0.35 g, 0.90 mmol) was taken up in ethyl acetate (9.0 ml). To this mixture was added SnCl2.2H2O (1.02 g, 4.50 mmol) and the reaction was heated under nitrogen at reflux for 1 h. The mixture was poured onto ice, the solution was made basic using NaHCO3 and the product was extracted into ethyl acetate several times (7-8). The ethyl acetate fractions were combined washed with brine and dried over Na2SO4 and the solvent was removed in vacuo to give 0.24 g (73.4%) of yellow solid. 1H NMR (CDCl3) 1.58-1.70 (1H, m), 1.80-1.92 (1H, m), 1.98 (3H, s), 2.06 (2H, t, J=7.7 Hz), 3.62 (3H, s), 4.00 (2H, br s), 4.56-4.63 (1H, m), 5.84 (1H, d, J=7.7 Hz), 6.50 (1H, s), 6.61 (1H, d, J=8.4 Hz), 7.29-7.42 (5H, m), 7.58 (1H, d, J=8.3 Hz); 13C NMR (CDCl3) 15.02, 29.25, 31.25, 51.57, 52.15, 113.27, 115.88, 123.52, 127.56, 128.37, 128.44, 130.92, 140.66, 141.44, 148.53, 168.58, 171.91.

Workup

  1. temperaturethe reaction was heated under nitrogen
  2. temperatureat reflux for 1 h
  3. additionThe mixture was poured onto ice
  4. extractionthe product was extracted into ethyl acetate several times (7-8)
  5. washThe ethyl acetate fractions were combined washed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1054bfbb27964055bffe74a02b84019a
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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