Triphenylphosphine → 4-Chloro-N-(6-methoxy-pyridin-3-ylmethyl)-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 851975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851975
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO[C:22]1[CH:23]=[CH:24][C:25](CO)=[N:26][CH:27]=1.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=N[C:51](OC(C)C)=[O:52]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:30][C:22]2[CH:27]=[N:26][C:25]([O:52][CH3:51])=[CH:24][CH:23]=2)[C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 69279554-Chloro-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamideHCID 12214020(5-Methoxypyridin-2-yl)methanol

Produkt 1

HCID 671950924-Chloro-N-(6-methoxy-pyridin-3-ylmethyl)-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Chloro-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide (0.04 g, 0.12 mmol), (5-Methoxy-pyridin-2-yl)-methanol (0.04 g, 030 mmol), triphenyl phosphine (0.08 g, 0.30 mmol) were dissolved in dry CH2Cl2 (6 ml) under an argon atmosphere followed by the dropwise addition of diisopropyl azodicarboxylate (60 mg, 0.30 ml) in dry CH2Cl2 (2 ml). The reaction mixture was further stirred overnight at r.t. and then concentrated under reduced pressure. The crude yellow oil was purified over silica gel (ethyl acetate/n-heptane 3:2): colorless gum 0.23 g (43%); MS: m/e=424.0 (MH+), 446.0 (MNa+).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe crude yellow oil was purified over silica gel (ethyl acetate/n-heptane 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-7355844456144f61aa10ea567e07defe
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253158B2

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