Benzene, 1-azido-4-chloro- → (S)-tert-butyl(1-(1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)ethyl)carbamate

HRID 57409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57409
[CH3:1][C@H:2]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]#[CH:4].[N:13]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)=[N+:14]=[N-:15].C(N(C(C)C)C(C)C)C>C(#N)C.[Cu]I>[C:8]([O:7][C:6](=[O:12])[NH:5][C@H:2]([C:3]1[N:15]=[N:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:4]=1)[CH3:1])([CH3:11])([CH3:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 76803Benzene, 1-azido-4-chloro-HCID 81531DiisopropylethylamineHCID 10986677tert-Butyl (2S)-but-3-yn-2-ylcarbamate

Produkt 1

HCID 90451725(S)-tert-butyl(1-(1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)ethyl)carbamateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of (S)-tert-butyl but-3-yn-2-ylcarbamate (250 mg, 1.48 mmol), 1-azido-4-chlorobenzene (227 mg, 1.48 mmol, 1.0 equiv), and N-ethyl-N-isopropylpropan-2-amine (0.77 mL, 4.43 mmol, 3.0 equiv) in anhydrous acetonitrile (14.8 mL) was stirred at room temperature for 10 min. Copper(I) iodide (563 mg, 2.95 mmol, 2.0 equiv) was then added in portions. The mixture was stirred at room temperature for 30 min. The reaction was quenched with saturated aqueous ammonium chloride (50 mL) and diluted with water (50 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic extracts were washed with water (30 mL), saturated aqueous sodium chloride (30 mL), dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane) provided (S)-tert-butyl(1-(1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)ethyl)carbamate (0.428 g, white solid) in 90% yield. 1H NMR (400 MHz, CDCl3) δ 7.86 (s, 1H), 7.68 (d, J=8.8 Hz, 2H), 7.50 (d, J=8.8 Hz, 2H), 5.02 (m, 1H), 1.63 (d, J=6.8 Hz, 3H), 1.46 (s, 9H). MS m/z 323.1 (M+H)+; Rt-0.92 min.

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous ammonium chloride (50 mL)
  2. additiondiluted with water (50 mL)
  3. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  4. washthe combined organic extracts were washed with water (30 mL), saturated aqueous sodium chloride (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5e4a89ed03e442eba8dfb26719092096
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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