Piperidine → (R)-4-thiocarbamoyl-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-isopropyl-benzylamide

HRID 908583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908583
Cl.[CH:2]([C:5]1[CH:33]=[CH:32][C:8]([CH2:9][NH:10][C:11]([C@H:13]2[CH2:18][NH:17][CH2:16][CH2:15][N:14]2[S:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[O:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C(N(CC)CC)C.C1C2C(COC([N:58]=[C:59]=[S:60])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C(Cl)(Cl)Cl>[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11]([C@H:13]2[CH2:18][N:17]([C:59](=[S:60])[NH2:58])[CH2:16][CH2:15][N:14]2[S:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[O:12])=[CH:32][CH:33]=1)([CH3:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 4154759Fmoc isothiocyanateHCID 67410019(R)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-isopropyl-benzylamide hydrochloride

Produkt 1

HCID 25055531(R)-4-thiocarbamoyl-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-isopropyl-benzylamideAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of the compound (506 mg) obtained in Example 1 in chloroform (5 ml) was added, with stirring at room temperature, triethylamine (167 μl), and 9-fluorenylmethoxycarbonyl isothiocyanate (281 mg) was added. After stirring overnight at room temperature, piperidine (198 μl) was added. After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure, and purified by column chromatography (3% methanol/chloroform) to give the title compound (442 mg).

Aufarbeitung

  1. stirringAfter stirring overnight at room temperature
  2. stirringAfter stirring overnight at room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. custompurified by column chromatography (3% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-c50f0c7599af4c2189a7a95659c8c342
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017612B2

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