p-Toluenesulfonic acid → HCID 69600972, Verbindung

HRID 2215088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215088
[O:1]=[C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14])[C@@H:5]([CH2:15][O:16]C2CCCCO2)[CH2:4][S:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CCO>[OH:16][CH2:15][C@H:5]1[CH2:4][S:3][C:2](=[O:1])[N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 69601148HCID 69601148, Verbindung

Produkt 1

HCID 69600972HCID 69600972, VerbindungAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-1 (0.97 g, 3.0 mmol) in 10 mL EtOH was added p-toluene sulfonic acid (50 mg) and the resulting solution was stirred overnight at room temperature. Triethylamine (0.1 mL) was added and the solution was concentrated in vacuo. The compound was purified by flash chromatography using 50–80% EtOAc/hexanes to yield 0.65 g of 4-2 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.92–3.73 (m, 3H), 3.68–3.60 (m, 1H), 3.42 (dd, 1H), 3.28 (dd, 1H), 3.10 (m, 1H), 2.37(t, 2H), 1.71–1.46 (m, 6H), 1.39–1.33 (m, 2H); MS (+ESI): m/z 243.1 (M+1)+.

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo
  2. customThe compound was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6ec3c79fb50d4fe089e24f14dc468379
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109223B2

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