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(Diethylamino)sulfur trifluoride → (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-fluoro azetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1051725
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Reaktionsgleichung

Reaktionsgleichung von HRID 1051725
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:14][C:15]([N:17]1[CH2:20][C:19]([C:22]2[S:23][CH:24]=[C:25]([C:27]3[C:28]([O:42][CH:43]4[CH2:46][CH2:45][CH2:44]4)=[C:29]4[C:34](=[CH:35][CH:36]=3)[N:33]([C:37]([O:39][CH3:40])=[O:38])[C@@H:32]([CH3:41])[CH2:31][CH2:30]4)[N:26]=2)(O)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+]>ClCCl>[C:10]([O:14][C:15]([N:17]1[CH2:20][C:19]([C:22]2[S:23][CH:24]=[C:25]([C:27]3[C:28]([O:42][CH:43]4[CH2:46][CH2:45][CH2:44]4)=[C:29]4[C:34](=[CH:35][CH:36]=3)[N:33]([C:37]([O:39][CH3:40])=[O:38])[C@@H:32]([CH3:41])[CH2:31][CH2:30]4)[N:26]=2)([F:7])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]
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Komponenten

5

Edukt 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 118076304(S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-hydroxyazetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

Produkt 1

HCID 118075426(S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-fluoro azetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(Diethylamino)sulfur trifluoride (DAST) (0.152 g, 0.94 mmol) was added to a −78° C. solution of (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-hydroxyazetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.100 g, 0.19 mmol) in dichloromethane (4 mL), and the resulting solution stirred for 2 h at −78° C. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution (20 mL) and extracted with dichloromethane (3×20 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via preparative thin layer chromatography (eluting with 30% ethyl acetate/petroleum ether) to afford (S)-methyl 6-(2-(1-(tert-butoxycarbonyl)-3-fluoro azetidin-3-yl)thiazol-4-yl)-5-cyclobutoxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate (0.059 g, 59%) as a yellow solid. MS (ESI, pos. ion) m/z 532 [M+H]+.

Aufarbeitung

  1. extractionextracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified via preparative thin layer chromatography (eluting with 30% ethyl acetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-8a94e2ec00bf472eb695fc4f75843269
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388161B2

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