Water → 8-Azetidin-3-yl-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1849450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1849450
C(OC([N:8]1[CH2:11][CH:10]([C:12]2[CH:34]=[CH:33][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:30]([CH3:32])[CH3:31])[N:26]=[C:27]([CH3:29])[N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.O.C(OCC)(=O)C>C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([C:12]2[CH:34]=[CH:33][C:15]3[C:16]4[N:17]=[C:18]([C:24]5[N:25]([CH:30]([CH3:32])[CH3:31])[N:26]=[C:27]([CH3:29])[N:28]=5)[S:19][C:20]=4[CH2:21][CH2:22][O:23][C:14]=3[CH:13]=2)[CH2:9]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 582040483-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 582041048-Azetidin-3-yl-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azuleneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carboxylic acid tert-butyl ester (4.11 g, 0.01234 mol) in methylene chloride (42 mL) was added trifluoroacetic acid (20 mL) dropwise. The reaction was stirred at room temperature for 1 hour. Water and ethyl acetate were added and the mixture was extracted with 1N HCl. The aqueous phase was basified to pH 13 with 1N NaOH. The aqueous phase was filtered and rinsed with cold water to afford 8-azetidin-3-yl-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene as an off-white solid (3.2 g). MS(ESI+) 382.2

Aufarbeitung

  1. extractionthe mixture was extracted with 1N HCl
  2. filtrationThe aqueous phase was filtered
  3. washrinsed with cold water

Quellen und Nachweise

ORD-Eintrag
ord-10448e5dd4c34565a62e2944920c4873
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952043B2

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