2-(5-Cyanopentyl)-2-(3-methyl[1,2,4]thiadiazol-5-yl)malonic acid di-tert-butyl ester → 7-Cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid

HRID 1639573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639573
C([O:5][C:6](=[O:28])[C:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])([C:15]1[S:19][N:18]=[C:17]([CH3:20])[N:16]=1)C(OC(C)(C)C)=O)(C)(C)C>FC(F)(F)C(O)=O>[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:7]([C:15]1[S:19][N:18]=[C:17]([CH3:20])[N:16]=1)[C:6]([OH:28])=[O:5])#[N:27]

Komponenten

3

Edukt 1

HCID 667221752-(5-Cyanopentyl)-2-(3-methyl[1,2,4]thiadiazol-5-yl)malonic acid di-tert-butyl ester

Produkt 1

HCID 593780557-Cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To stirred trifluoroacetic acid (20 mL) was added 2-(5-cyanopentyl)-2-(3-methyl[1,2,4]thiadiazol-5-yl)malonic acid di-tert-butyl ester (2021051) (0.75 g, 1.83 mmol) and the resultant mixture was stirred at room temperature for 1.5 h. The TFA was then removed under reduced pressure, while the temperature of the water bath was maintained below 25° C. The resultant oil was dissolved in dichloromethane (20 mL) and made basic with the careful addition of triethylamine, while keeping the reaction temperature below 20° C. The dichloromethane solution of 7-cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid (2021052) was then immediately used in the next step.

Aufarbeitung

  1. customThe TFA was then removed under reduced pressure, while the temperature of the water bath
  2. temperaturewas maintained below 25° C
  3. dissolutionThe resultant oil was dissolved in dichloromethane (20 mL)
  4. additionmade basic with the careful addition of triethylamine
  5. customthe reaction temperature below 20° C

Quellen und Nachweise

ORD-Eintrag
ord-e5ce67f66b994123904bfe569262d765
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110577B2

Notizen zur Reaktion

Wird geladen…