StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethyl-1,3-thiazole-5-carboxylic acid → 2-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acid

HRID 1923573
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1923573
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Li]CCCC.[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:27]([CH:28]=[O:29])=[C:26]([CH3:30])[O:25][N:24]=2)=[N:21][CH:22]=1>C1COCC1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:27]([CH:28]([OH:29])[CH2:1][C:2]3[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=3)=[C:26]([CH3:30])[O:25][N:24]=2)=[N:21][CH:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 866472723-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 666437052-{2-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-2-hydroxy-ethyl}-4-methyl-thiazole-5-carboxylic acidAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a stirred solution of 2,4-dimethyl-thiazole-5-carboxylic acid (650 mg, 7.0 mmol) in THF (33 mL) at −70° C. and under argon was added BuLi (1.6M in hexanes, 4.94 mL, 7.9 mmol) dropwise. After 2 h a solution of 3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazole-4-carbaldehyde (814 mg, 3.95 mmol) in THF (12 mL) was added dropwise. After 2 h the reaction mixture was quenched with citric acid solution (5%, 25 mL) then warmed to room temperature and extracted with ethyl acetate. The combined extracts were washed with brine, water, dried over sodium sulfate, filtered and concentrated. Purification by recrystallization (ethyl acetate) afforded the title compound (729 mg, 51%) as a light yellow solid. MS: m/e=362.2 [M+H]+.

Aufarbeitung

  1. customAfter 2 h the reaction mixture was quenched with citric acid solution (5%, 25 mL)
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine, water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. customby recrystallization (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-07c00ccfa2b840d5a9a28440a16892b1
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08178522B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion