Cesium carbonate → Diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]malonate

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Reaktionsgleichung

C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)=[O:13])([CH3:10])([CH3:9])[CH3:8].[C:20]1([CH3:45])[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH:33]=[C:32]([CH:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:31]=[CH:30]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1>CN(C=O)C>[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:34]([C:32]1[N:31]=[CH:30][N:29]([S:26]([C:23]2[CH:22]=[CH:21][C:20]([CH3:45])=[CH:25][CH:24]=2)(=[O:27])=[O:28])[CH:33]=1)([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

13.7 g (42.0 mmol) of cesium carbonate and 3.24 g (11.56 mmol) of 4-(t-butyloxycarbonylamino)butyl bromide were added to a solution of 4.0 g (10.51 mmol) of diethyl 2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]malonate in 67 ml of DMF, and the mixture was stirred at 60° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was taken up in ethyl acetate and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated. Chromatography on silica gel (heptane/ethyl acetate 1:1) gave the title compound (4.21 g, 73%). LC/MS: Rt=2.08 min, [M+H]+=552, (method A).

Aufarbeitung

concentrationThe reaction mixture was concentrated under reduced pressure
washwashed with water
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-70aa9ed8f4854dcab21e3699d4b6412b
Quelldatensatz: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08044208B2

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