4-Chlorobenzenesulfonyl chloride → 1,1-Dimethylethyl (3S)-4-[(4-chlorophenyl)sulfonyl]-3-methyl-1-piperazinecarboxylate

HRID 41293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41293
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@@H:2]2[CH3:1])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 7023035(S)-1-Boc-3-methylpiperazine

Produkt 1

HCID 582844531,1-Dimethylethyl (3S)-4-[(4-chlorophenyl)sulfonyl]-3-methyl-1-piperazinecarboxylateAusbeute 129 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl (3S)-3-methyl-1-piperazinecarboxylate (10.0 g, 49.9 mmol, supplier Aldrich) in pyridine (30 ml) was added 4-chlorobenzenesulfonyl chloride (12.7 g, 59.9 mmol) portionwise. The reaction was stirred at room temperature under an argon atmosphere for 2 hours. The reaction was then evaporated, partitioned between 2N aq. HCl (70 ml) and DCM (80 ml). The aqueous was further extracted with DCM (2×80 ml) and the combined DCM layers were passed through a hydrophobic frit and evaporated. The product was dried under vacuum at 40° C. for 18 hours to yield the title compound as an orange solid (24.14 g).

Aufarbeitung

  1. customThe reaction was then evaporated
  2. custompartitioned between 2N aq. HCl (70 ml) and DCM (80 ml)
  3. extractionThe aqueous was further extracted with DCM (2×80 ml)
  4. customevaporated
  5. customThe product was dried under vacuum at 40° C. for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-3690e5acb53048c9a34256f8859085f1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530478B2

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