Acetic Anhydride → HCID 68411356, Verbindung

HRID 1523445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1523445
[OH:1][CH:2]1[CH:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[CH2:4][CH:3]1[CH3:25].[CH3:26][C:27](OC(C)=O)=[O:28]>N1C=CC=CC=1>[C:27]([O:1][CH:2]1[CH:3]([CH3:25])[CH2:4][C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])=[CH:6][CH:7]1[NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:15])(=[O:28])[CH3:26]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 67135398Tert-butyl 6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

Produkt 1

HCID 68411356HCID 68411356, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of (+/−)-tert-butyl 6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.) in pyridine (0.1 M) was added Ac2O (2.0 equiv.) and the reaction was stirred at room temperature overnight. Upon completion, the reaction was concentrated to dryness, then worked-up with ethyl acetate and water. The organic phase was dried with brine, then sodium sulfate, filtered, and concentrated to give (+/−)-2-(tert-butoxycarbonylamino)-6-methyl-4-(3-nitropyridin-4-yl)cyclohex-3-enyl acetate in 94% yield. LC/MS=392.2 (M+H), Rt=0.94 min.

Aufarbeitung

  1. concentrationUpon completion, the reaction was concentrated to dryness
  2. dry with materialThe organic phase was dried with brine
  3. filtrationsodium sulfate, filtered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9ba86372e00a46d095974c489967ccdc
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079889B2

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