Ammonia → HCID 58124845, Verbindung

HRID 1971734Notizen

Reaktionsgleichung

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15](=O)[C:16](N(C(C)(C)C)CCCCC#C)=[O:17])[CH:9]2[C:12](O)=O)=[CH:4][C:3]=1[O:30][CH3:31].[C:32]([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.[NH3:44].CC[CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].C(O[CH:56]([CH3:58])[CH3:57])(C)C>O>[C:56]([N:44]1[CH2:47][CH2:48][CH2:49][CH2:50][C:51]2[CH:12]=[C:9]3[C:10]4[CH:11]=[C:2]([Br:1])[C:3]([O:30][CH3:31])=[CH:4][C:5]=4[CH2:6][CH2:7][N:8]3[C:15]=2[C:16]1=[O:17])([CH3:58])([CH3:32])[CH3:57]

Komponenten

Reaktionsbedingungen

Temperatur: 105 °C

Versuchsvorschrift

A mixture of 420 g of 19c and 500 mg of sodium acetate and 8 ml of acetic anhydride was heated at 105° C. for 3 h. The reaction mixture was cooled and diluted with 20 ml of water and stirred for 1 h to decompose the acetic anhydride. Then a solution of cold conc. ammonia was added to pH 8. The product was extracted with ethyl acetate. The organic layer was washed, dried, concentrated and the crude material was chromatographed over silica gel, using a gradient of heptane/ethyl acetate as eluent. The material thus isolated was treated with heptane/diisopropyl ether (1/1) to provide 95 mg of 19d as white crystalline material; Mp 127-129° C.

Aufarbeitung

temperatureThe reaction mixture was cooled
extractionThe product was extracted with ethyl acetate
washThe organic layer was washed
customdried
concentrationconcentrated
customthe crude material was chromatographed over silica gel
customThe material thus isolated

Quellen und Nachweise

ORD-Eintrag: ord-b7aff978435241788a244200db87c1ef
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08431564B2

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