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

Sodium Hydroxide → 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid

HRID 2381390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2381390
C[O:2][C:3](=[O:27])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[N:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[N:20]=2)[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>O1CCCC1>[CH:6]1([CH2:5][CH:4]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[N:20]=[C:21]([CH3:26])[CH:22]=[C:23]([CH3:25])[N:24]=3)[CH:13]=[N:12]2)[C:3]([OH:27])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 668750953-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester

Produkt 1

HCID 579191953-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acidAusbeute 20,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (206 mg, 0.55 mmol) in tetrahydrofuran (4 mL) was treated with a 4N aqueous sodium hydroxide solution (0.17 mL) and was stirred at 25° C. for 4 h. The reaction was partitioned between water (3 mL) and ether. The aqueous layer was back extracted with ether. The aqueous layer was then acidified to pH 3-4 with a 1N aqueous hydrochloric acid solution. The resulting precipitate was filtered, rinsed with water (1 mL), and dried in vacuo to afford 3-cyclopentyl-2-[4-(4,6-dimethyl-pyrimidin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (40 mg, 20%); LC-MS: tR=3.71 min, 359 [M+H]+. HPLC: tR=7.02 min, 96.21% at 214 nm, 98.34% at 254 nm. 1H NMR (300 MHz, DMSO-d6): δ13.03 (broad, 1H), 8.12 (d, 1H, J=2.7 Hz), 7.19 (s, 1H), 6.85 (d, 1H, J=2.4 Hz), 5.36 (dd, 1H, J=10.5 Hz, J=4.2 Hz), 2.41 (s, 6H), 2.24-2.14 (m, 1H), 2.05-1.97 (m, 1H), 1.71-1.44 (m, 7H), 1.17-1.04 (m, 2H).

Aufarbeitung

  1. customThe reaction was partitioned between water (3 mL) and ether
  2. extractionThe aqueous layer was back extracted with ether
  3. filtrationThe resulting precipitate was filtered
  4. washrinsed with water (1 mL)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4ac8552bea3041bc895ccc3ccab10a3e
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08258134B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion