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

Lithium Hydroxide → [3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid

HRID 660902
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 660902
C[O:2][C:3](=[O:25])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:6]1.[OH-].[Li+]>CO.O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:7]2[N:8]([CH2:11][CH:12]([OH:17])[C:13]([F:16])([F:14])[F:15])[C:9](=[O:10])[N:5]([CH2:4][C:3]([OH:25])=[O:2])[N:6]=2)=[CH:19][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 58011736Methyl {3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetate

Produkt 1

HCID 58011686[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

The enantiomerically pure ester from Example 227A (265 mg, 0.70 mmol) is dissolved in 14 ml methanol and treated with 2.8 ml of a 1 M solution of lithium hydroxide in water. The mixture is stirred for 1 hr at RT and then freed of methanol on the rotary evaporator. The residue is diluted with 200 ml water and extracted once with dichloromethane. This organic phase is discarded. The aqueous phase is slowly acidified to pH 2 with 1 N hydrochloric acid. The product is extracted three times with dichloromethane, the combined organic phases are dried over sodium sulphate and the solvent removed on the rotary evaporator. The residue is dried under high vacuum. 142 mg (56% of theory) of the title compound are thus obtained. Since the aqueous phase still contains more product, it is evaporated to dryness on the rotary evaporator, and the residue is dissolved in a little DMSO and purified by preparative HPLC (Method 20). A further 71 mg (28% of theory) of the pure title compound are obtained.

Aufarbeitung

  1. customfreed of methanol on the rotary evaporator
  2. additionThe residue is diluted with 200 ml water
  3. extractionextracted once with dichloromethane
  4. extractionThe product is extracted three times with dichloromethane
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. customthe solvent removed on the rotary evaporator
  7. customThe residue is dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3adc564136c24438a7bd801e421ddb0d
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084481B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion