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

HRID 1739138
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1739138
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 18666758N-(4-Amino-2-phenylbenzoyl)methionine methyl esterAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1054bfbb27964055bffe74a02b84019a
Quelldatensatz
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05965539

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