Water → HCID 178451419, Verbindung

HRID 1846814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846814
[C:1]([O:5][C:6](O[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([O:23][CH:24]1[CH2:27][CH:26]([C:28]2[NH:32][C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][C:30]=3[N:29]=2)[CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.ClCCl>[CH2:16]([O:23][C@@H:24]1[CH2:25][C@H:26]([C:28]2[N:29]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1.[CH2:16]([O:23][C@H:24]1[CH2:25][C@H:26]([C:28]2[N:29]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=2)[CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 674813742-(3-(Benzyloxy)cyclobutyl)-1H-benzo[d]imidazole

Produkt 2

HCID 178451418HCID 178451418, VerbindungAusbeute 33 %HCID 178451419HCID 178451419, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

DMAP (0.020 g, 0.16 mmol) and di-tert-butyldicarbonate (0.83 g, 3.77 mmol) were added to a suspension of 2-(3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole (0.96 g, 3.43 mmol) and triethylamine (1.20 mL, 8.58 mmol) in dichloromethane (15 mL) and the mixture was stirred for 16 h. Water was added, the resulting layers were separated, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography to give tert-butyl 2-(cis-3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.43 g, 1.14 mmol, 33% yield) and tert-butyl 2-(trans-3-(benzyloxy)cyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.47 g, 1.23 mmol, 36% yield).

Aufarbeitung

  1. customthe resulting layers were separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-79b2e34ebfbd4da7b5cd48404d1fa16e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952037B2

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