Sodium Hydroxide → 5-(Cyclopropylcarbamoyl)isoxazole-3-carboxylic acid

HRID 1409382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409382
[CH:1]1([NH:4][C:5]([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14]CC)=[O:13])[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([NH:4][C:5]([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=2)=[O:6])[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 70980010Ethyl 5-(cyclopropylcarbamoyl)isoxazole-3-carboxylate

Produkt 1

HCID 867146445-(Cyclopropylcarbamoyl)isoxazole-3-carboxylic acidAusbeute 23,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 5-(cyclopropylcarbamoyl)isoxazole-3-carboxylate (1.267 mmol, 0.284 g) was dissolved in ethanol (10 ml). The mixture was cooled in an ice bath and NaOH 2 M solution (2.53 mmol, 1.267 ml) was added. The resulting mixture was stirred in cold until the reaction was complete. Ethanol was evaporated and water was added. The pH of the mixture was adjusted to 4 with HCl. The precipitate was removed by filtration. The filtrate was evaporated and purified by trituration from 1/9 MeOH/DCM. 0.058 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 0.57-0.66 (m, 2H), 0.67-0.75 (m, 2H), 2.77-2.88 (m, 1H), 6.97 (s, 1H), 8.85 (m, 1H).

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. customEthanol was evaporated
  3. additionwater was added
  4. customThe precipitate was removed by filtration
  5. customThe filtrate was evaporated
  6. custompurified by trituration from 1/9 MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-00dfd005e1c3499598309e740d97b4fb
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921378B2

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