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Triethylamine → 2-[4-(4-Phenyl-1H-imidazole-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamate

HRID 967807
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 967807
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:26]1([C:32]2[N:33]=[CH:34][NH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:13])[O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N:35]3[CH:36]=[C:32]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:33]=[CH:34]3)=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 218765304-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acidHCID 178418822HCID 178418822, Verbindung

Produkt 1

HCID 98471322-[4-(4-Phenyl-1H-imidazole-1-YL)phenyl]ethyl (4-methylphenyl)sulfonylcarbamateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895
Cupric acetate
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-{2-[({[(4-Methylphenyl)sulfonyl]amino}carbonyl)oxy]ethyl}phenylboronic acid (100 mg, 0.28 mmol), 4-phenylimidazole (40 mg, 0.28 mmol), Copper(II) acetate (50 mg, 0.28 mmol), triethylamine (115 μL, 0.83 mmol), molecular sieves 4A (100 mg), and dichloromethane (4 mL) was stirred at room temperature for 1 week. Insoluble materials were removed by Celite pad, the filtrate was diluted with dichloromethane, and washed with water. The combined organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by TLC with dichloromethane/methanol (10:1) to afford 58 mg (46%) of the title compound as white solids: MS (ESI) m/z 462 [M+H]+, 460 [M−H]−, 1H-NMR (DMSO-d6) δ 2.35 (3H, s), 2.88 (2H, t, J=6.5 Hz), 4.23 (2H, t, J=6.5 Hz), 7.22-7.43 (7H, m), 7.62 (2H, d, J=8.3 Hz), 7.74 (2H, d, J=8.3 Hz), 7.86 (2H, d, J=7.3 Hz), 8.26 (1H, s), 8.32 (1H, s).

Aufarbeitung

  1. customInsoluble materials were removed by Celite pad
  2. additionthe filtrate was diluted with dichloromethane
  3. washwashed with water
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by TLC with dichloromethane/methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-0e24fd68fde4490bb26a2095943084cf
Quelldatensatz
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06956050B2

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