Hydrochloric Acid → (+/-)-2-Amino-3-(3,4-dichloro-phenyl)-3-oxo-propionic acid methyl ester hydrochloride
Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1[N:6]=C[O:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[O:4].Cl>CO>[ClH:16].[CH3:1][O:2][C:3](=[O:4])[CH:5]([NH2:6])[C:9]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[O:8]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
A suspension of 5-(3,4-dichloro-phenyl)-oxazole-4-carboxylic acid methyl ester (1.5 g, 5.51 mmol), 3 N HCl (10 mL), and MeOH (15 mL) was heated at 50° C. for 4 h. The mixture was concentrated, diluted with water, and washed with Et2O. The aqueous layer was concentrated and Et2O was added, causing precipitation of a white solid. The precipitate was collected by filtration to provide 1.0 g (63%) of the desired product as an apparent 10:1 mixture of keto-enol tautomers. MS (ESI+): mass calcd. for C10H9Cl2NO3, 261.00; m/z found, 262/264 [M+H]+. Major tautomer: 1H NMR (500 MHz, CDCl3): 8.32 (d, J=2.1, 1H), 8.09 (dd, J=8.4, 2.1, 1H), 7.79 (d, J=8.5, 1H), 3.80 (s, 3H). Minor tautomer: 1H NMR (500 MHz, CDCl3): 8.19 (d, J=2.0, 1H), 7.96 (dd, J=8.4, 2.1, 1H), 7.76 (d, J=8.4, 1H), 6.18 (s, 1H).
Aufarbeitung
- concentrationThe mixture was concentrated
- additiondiluted with water
- washwashed with Et2O
- concentrationThe aqueous layer was concentrated
- additionEt2O was added
- customprecipitation of a white solid
- filtrationThe precipitate was collected by filtration
Quellen und Nachweise
- ORD-Eintrag
- ord-ab234983977d4db2ae56f77fe645d9c9
- Quelldatensatz
- uspto-grants-2010_12
- Patentnummer
- US07855292B2
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