Toluene → HCID 178455819, Verbindung

HRID 1694994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694994
N(C(OCC)=O)=N[C:3](OCC)=O.C1(C)C=CC=CC=1.O[CH2:21][C@H:22]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N+:40]([O-:42])=[O:41])(=[O:33])=[O:32])[C@@H:23]1[CH2:27][C@@H:26]([CH3:28])[C:25](=[O:29])[O:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:28]([C@@H:26]1[CH2:27][C@@H:23]([CH:22]2[CH2:21][N@@:30]2[S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])(=[O:33])=[O:32])[O:24][C:25]1=[O:29])[CH3:3]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66645672N-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

Produkt 1

HCID 178455819HCID 178455819, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.60 ml of a solution of diethyl azodicarboxylate in toluene (40%) (3.52 mmol) was added to a solution of 1.05 g of N-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide obtained in Example (106f) (2.93 mmol) and 923 mg of triphenylphosphine (3.52 mmol) in tetrahydrofuran (30 ml) under ice-cooling over five minutes, and the mixture was stirred at the same temperature for five minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1) to obtain 916 mg of the title compound (yield: 92%).

Aufarbeitung

  1. temperaturecooling over five minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-036a117069dc4949a11149e87d1c7b63
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158790B2

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