Ethyl Acetate → HCID 178519232, Verbindung

HRID 2215091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215091
[OH:1][CH:2]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18].C([Sn]([N:39]=[N+:40]=[N-:41])(CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:1][CH:2]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)/[CH:3]=[CH:4]/[C@H:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[NH:41][N:40]=[N:39][N:18]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 4984872Tributyltin azideHCID 69601022HCID 69601022, Verbindung

Produkt 1

HCID 178519232HCID 178519232, VerbindungAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-4 (70 mg, 0.2 mmol) in 0.2 mL toluene was added tributyltin azide (0.27 mL, 1.0 mmol) and the resulting solution was stirred at reflux for 4 hours. Ethyl acetate (100 mL) was added and the solution was quenched with 5% aqueous KF (30 mL) and 1N HCl (30 mL). The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 0–5% MeOH/CH2Cl2 to yield 50 mg of 4-5 as a colorless oil. 1H NMR (400 MHz, CD3OD): δ7.29–7.17 (m, 5H), 5.81 (dd, 1H), 5.53 (dd, 1H), 4.38 (q, 1H), 4.33 (q, 1H), 3.45 (dd, 1H), 3.33 (m, 1H), 2.97 (m, 4H), 2.78 (m, 1H), 2.68 (m, 1H), 1.83–1.21 (m, 8H); MS (−ESI): m/z 400.2 (M−1)−.

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. customthe solution was quenched with 5% aqueous KF (30 mL) and 1N HCl (30 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe compound was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-455b260ecb844ff58982bdd80aa89ac1
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109223B2

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