Lawesson's reagent → tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate

HRID 10952

Reaktionsgleichung

Reaktionsgleichung von HRID 10952
O=[C:2]1[NH:6][C@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1C=CC=CC=1>[S:23]=[C:2]1[NH:6][C@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 10888648tert-Butyl 5-oxo-L-prolinate

Produkt 1

HCID 14416882tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylateAusbeute 191,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of t-butyl pyroglutamate (1a) (10.12 g, 54.6 mmol) in benzene (250 mL), was added Lawesson's reagent (11.05 g, 27.3 mmol). The mixture was stirred at reflux for 15.5 h, then concentrated. The resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3) to afford 10.50 g (95%) of the title compound, 1b. 1H NMR (300 MHz, CDCl3) δ 7.27 (br s, 1H), 4.46–4.39 (m, 1H), 3.03–2.84 (m, 2H), 2.58–2.46 (m, 1H), 2.37–2.23 (m, 2H), 1.49 (s, 9H).

Aufarbeitung

  1. temperatureat reflux for 15.5 h
  2. concentrationconcentrated
  3. customThe resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-585925510a744f649fc62878129472d8
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094783B2

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