Hydrochloric Acid → (3-((3-(4-(2,2-Dimethoxyethyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)-(phenyl)methanamine

HRID 332698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332698
Cl.O1CCOCC1.C(OC(=O)[NH:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:29][C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][CH:42]4[O:46][CH2:45][CH2:44][O:43]4)=[CH:37][CH:36]=3)[N:31]=2)[CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C>CO>[CH3:45][O:46][CH:42]([O:43][CH3:44])[CH2:41][C:38]1[CH:37]=[CH:36][C:35]([C:32]2[N:31]=[C:30]([CH2:29][O:28][C:24]3[CH:23]=[C:22]([CH:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH2:14])[CH:27]=[CH:26][CH:25]=3)[O:34][N:33]=2)=[CH:40][CH:39]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71113095Tert-butyl((3-((3-(4-((1,3-dioxolan-2-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate

Produkt 1

HCID 86676912(3-((3-(4-(2,2-Dimethoxyethyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)-(phenyl)methanamineAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Hydrogen chloride in dioxan (4.0 M, 5 mL, 24 mmol) was added to a solution of tert-butyl((3-((3-(4-((1,3-dioxolan-2-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate (1.01 g, 1.85 mmol) in methanol (5 mL), and the resultant solution was stirred at ambient temperature for 2 hours. The solvent was evaporated at reduced pressure, and the residue was loaded onto an SCX-2 cartridge. The cartridge was eluted with methanol (eight column volumes) followed by ammonia/methanol. Fractions containing the product were combined and evaporated at reduced pressure to afford the title compound (0.796 g, 96%).

Aufarbeitung

  1. customThe solvent was evaporated at reduced pressure
  2. washThe cartridge was eluted with methanol (eight column volumes)
  3. additionFractions containing the product
  4. customevaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ac8db9a0604949fa8d40691f565cb010
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

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