Ethanol → tert-Butyl 2-(3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)butanoate

HRID 1765647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765647
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][C@@H:16]1[CH2:20][CH2:19][N:18]([C@H:21]([CH3:29])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]1=[O:30])(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH2:31](O)C.C(NC(C)C)(C)C>[Pd].C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([NH:15][CH:16]1[CH2:20][CH2:19][N:18]([CH:21]([CH2:29][CH3:31])[C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:17]1=[O:30])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 702EthanolHCID 7912DiisopropylamineHCID 69222335tert-Butyl(2R)-2-((3R)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

Produkt 1

HCID 22017281tert-Butyl 2-(3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of Intermediate 112 [Mixture 1] (0.051 g), 10% palladium on carbon (0.01 g) and ethanol (5 ml) was stirred under an atmosphere of hydrogen for 18 h. The reaction mixture was filtered through Celite™ and the filtrate was concentrated under reduced pressure to give a yellow gum. The gum (0.034 g) in DCM (2 ml) was treated with 6-chloronaphthylsulphonyl chloride1 (0.04 g) and N,N-diisopropylamine (0.073 ml) and stirred at room temperature for 24 h. The mixture was washed with water and concentrated under reduced pressure to yield an oil which was partially purified using SPE (silica, eluting with cyclohexane:ethyl acetate 1:1) to give the title compound (0.043 g) as a white solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite™
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a yellow gum
  4. stirringstirred at room temperature for 24 h
  5. washThe mixture was washed with water
  6. concentrationconcentrated under reduced pressure
  7. customto yield an oil which
  8. customwas partially purified
  9. washSPE (silica, eluting with cyclohexane:ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-f0a5a2f7defc4798b831fb93112ca5ed
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226929B2

Notizen zur Reaktion

Wird geladen…