Stannous chloride dihydrate → 4-Amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

HRID 1739144Notes

Reaction equation

HRID 1739144 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:25][CH2:26][S:27][CH3:28])[NH:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=1.O.O.Cl[Sn]Cl.COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1C1C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:29])[C@H:4]([CH2:25][CH2:26][S:27][CH3:28])[NH:5][C:6](=[O:24])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:16]1[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl esterHCID 186667634-Nitro-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

Product 1

HCID 186667574-Amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-nitro-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester (0.11 g, 0.26 mmol) was taken up in ethyl acetate (3.0 ml). To this mixture was added SnCl2.2H2O (0.30 g, 1.30 mmol) and the reaction was heated under nitrogen at reflux for 6 h. The mixture was worked up as described for 4-amino-2-phenylbenzoyl methionine methyl ester in Example 2, to give 0.15 g of a yellow film that was wet with solvent. The material was otherwise pure by NMR and was used without further purification. 1H NMR (CDCl3) 1.60-1.70 (1H, m), 1.80-1.90 (1H, m), 1.99 (3H, s), 2.05 (2H, t, J=7.6 Hz), 2.33 (6H, s), 3.64 (3H, s), 3.93 (2H, br s), 4.61-4.64 (1H, m), 5.82 (1H, d, J=7.7 Hz), 6.49 (1H, d, J=2.3 Hz), 6.62 (1H, dd, J=8.4 Hz, 2.4 Hz), 6.98 (2H, s), 7.00 (1H, s), 7.65 (1H, d, J=8.3 Hz); 13C NMR (CDCl3) 15.08, 21.17, 29.28, 31.49, 51.70, 52.18, 113.30, 115.94, 123.55, 126.36, 129.32, 131.23, 138.15, 140.72, 141.92, 148.40, 168.45, 172.01.

Workup

  1. temperaturethe reaction was heated under nitrogen
  2. temperatureat reflux for 6 h
  3. customto give 0.15 g of a yellow film that
  4. customwas used without further purification

Sources & evidence

ORD record
ord-24d6d8f55a9043dcbf1d5c6d1347d300
Source dataset
uspto-grants-1999_10
Patent number
US05965539

Reaction notes

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