Ethyl Acetate → {1-[4-(2-Phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037319

Reaktionsgleichung

Reaktionsgleichung von HRID 1037319
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=O)[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:45])=CC=1.CCOC(C)=O>C1(C)C=CC=CC=1.C1CCCCC1>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[S:45])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:20][C:19]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 8857Ethyl Acetate2×HCID 87949Lawesson's reagentHCID 67067804{1-[4-(4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 86671045{1-[4-(2-Phenyl-4-thioxo-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterAusbeute 185,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

To a solution of {1-[4-(4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (30 mg, 0.0642 mmol) in toluene (3 mL) was added Lawesson's reagent (2,4-bis-(4-methoxy-phenyl)-[1,3,2,4]dithiadiphosphetane 2,4-disulfide) (15.6 mg, 0.039 mmol). The reaction mixture was heated at reflux for 3 hours. The cooled mixture was subjected to flash chromatography (SiO2, 20% EtOAc in cyclohexane). A second chromatography (SiO2, 3% EtOAc in toluene) afforded the title compound (35 mg). LCMS (Method A): RT=5.08 min, [M+H]+=484.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours

Quellen und Nachweise

ORD-Eintrag
ord-fe1858bbca4646f1bb35de4b3f21fb73
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546376B2

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