Hydrochloric Acid → (S)-2-[(7-Hydroxy-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)amino]-propionic acid

HRID 2388170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388170
[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([O:10]CC)=O.[NH2:22][C@H:23]([C:25]([OH:27])=[O:26])[CH3:24].[O-]CC.[Na+].Cl>CN(C=O)C.O>[OH:1][C:2]1[C:3]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:4]=2[CH:5]=[N:6][C:7]=1[C:8]([NH:22][C@@H:23]([CH3:24])[C:25]([OH:27])=[O:26])=[O:10]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 2723922Sodium ethoxideHCID 67530168HCID 67530168, Verbindung

Produkt 1

HCID 42635755(S)-2-[(7-Hydroxy-3-phenyl-isoxazolo[4,5-c]pyridine-6-carbonyl)amino]-propionic acidAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl 7-hydroxy-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (0.1 g, 0.35 mmol) was dissolved in 10 mL of DMF. L-Alanine (0.627 g, 7.04 mmol) and sodium ethoxide (0.36 g, 5.28 mmol) were added and the mixture was refluxed for 3 h. The mixture was cooled to room temperature and diluted with 70 mL of water. Concentrated hydrochloric acid was added dropwise until pH was 2. The resulting suspension was filtered and the solid dried under vacuum to give 91 mg of the title compound. MS: (+) m/z 328.00 (M+1).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationThe resulting suspension was filtered
  3. customthe solid dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8f53663229d84adfa290d93211bbecc5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08269008B2

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