Lawesson's reagent → tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate

HRID 881688

Reaktionsgleichung

Reaktionsgleichung von HRID 881688
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([O:27][C:28]([N:30](C(OC(C)(C)C)=O)[C@@H:31]([C:45](O)=O)[CH2:32][CH2:33][C@@H:34]([C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:38]=1[F:44])[CH2:35][NH2:36])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[F:44][C:38]1[C:39]([F:43])=[CH:40][CH:41]=[CH:42][C:37]=1[C@H:34]1[CH2:35][NH:36][C:45](=[S:10])[C@H:31]([NH:30][C:28](=[O:29])[O:27][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:32][CH2:33]1

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 67526479(5S)-N2,N2-Bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-D-lysine2×

Produkt 1

HCID 59734935tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] (2.90 g, 7.18 mmol) was added to a suspension of tert-butyl (3R,6S)-6-(2,3-difluorophenyl)-2-oxoazepan-3-ylcarbamate (4.79 g, 14.1 mmol, described in Intermediate 4) in toluene (250 mL) and the mixture was heated to 90° C. After 1 h, the reaction was allowed to cool to ambient temperature and concentrated under reduced pressure. The residue was partially purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 85:15.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partially purified by silica gel chromatography
  4. washeluting with a gradient of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-c9376a80ce3b49bfb72afd36e1d192c4
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993588B2

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