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Heptane → (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate

HRID 2357099
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2357099
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][C:24]1([CH3:62])[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@:27]([CH3:61])([C:36]([NH:38][NH:39][C:40](=O)[C:41]2[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[C:43]([C:56]([F:59])([F:58])[F:57])[CH:42]=2)=O)[CH2:26][O:25]1.C([O-])(O)=O.[Na+].CCCCCCC>C1(C)C=CC=CC=1>[CH3:23][C:24]1([CH3:62])[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@:27]([CH3:61])([C:36]2[S:10][C:40]([C:41]3[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[C:43]([C:56]([F:59])([F:58])[F:57])[CH:42]=3)=[N:39][N:38]=2)[CH2:26][O:25]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8900HeptaneHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 53349361HCID 53349361, Verbindung

Produkt 1

HCID 59384428(R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylateAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
20.5 °C

Versuchsvorschrift

A 12 L, round bottom flask was inerted and charged with Lawesson's reagent (211.5 g, 0.52 mol, 1.2 equiv), a solution of (S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)benzoyl)-hydrazinecarbonyl)oxazolidine-3-carboxylate (D8A) (250 g—based on theoretical output, 0.43 mol) in toluene (2.5 L), and the resulting slurry was heated to 80° C. and held for 3 hours. TLC indicated the reaction was complete. The mixture was cooled to 18-23° C., charged with saturated NaHCO3 solution (2 L), which was slightly exothermic. The aqueous was extracted twice with ethyl acetate (2 L, 1.5 L), the organic phases were combined, concentrated, dissolved in dichloromethane (500 mL), charged with silica-gel (500 g), concentrated to remove dichloromethane, and purified using a silica-gel (2.5 kg) column which was eluted with 5% ethyl acetate: 95% heptane to afford the title product (185 g, 74% yield, 95% AUC by HPLC) as a yellow color oil.

Aufarbeitung

  1. extractionThe aqueous was extracted twice with ethyl acetate (2 L, 1.5 L)
  2. concentrationconcentrated
  3. dissolutiondissolved in dichloromethane (500 mL)
  4. additioncharged with silica-gel (500 g)
  5. concentrationconcentrated
  6. customto remove dichloromethane
  7. custompurified
  8. washwas eluted with 5% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-933497eeb29546d08273ba59cb2e9447
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759370B2

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