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

HRID 1739144노트

반응식

HRID 1739144 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-24d6d8f55a9043dcbf1d5c6d1347d300
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965539

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