Water → 2,4-dioxo-1,5-bis-(2,2-dimethylpropyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

HRID 133266

Reaktionsgleichung

O=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4](=[O:13])[CH2:3]1.[CH2:14](I)[C:15]([CH3:18])([CH3:17])[CH3:16].[C:20]([O-:23])([O-])=O.[Cs+].[Cs+].O>CS(C)=O.CCOC(C)=O>[O:13]=[C:4]1[N:5]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]([CH2:2][C:15]([CH3:17])([CH3:16])[CH3:14])[C:20](=[O:23])[CH2:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

To a stirred suspension of the product from Example 8-P, Step A (1.0 eq., 17.08 g) in DMSO (500 mL) at room temperature was added neopentyl iodide (43.01 g, 2.24 eq., Aldrich) and Cs2CO3 (72.65 g, 2.3 eq., Aldrich). The resulting mixture was heated to 75° C. for 30 minutes, then additional Cs2CO3 (31.59 g, 1.0 eq.) was added and the mixture rapidly stirred at 75° C. for 6 hours. The mixture was allowed to cool and H2O (500 mL) and EtOAc (1000 mL) were added. The phases were partitioned and the organic phase washed with H2O (1×500 mL), 1 M aq. HCl (2×500 mL), and brine (1×500 mL). Then, the organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography eluting with hexanes/EtOAc (3:2 gradient to 2:3) to provide 2,4-dioxo-1,5-bis-(2,2-dimethylpropyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine as a white solid.

Aufarbeitung

temperatureto cool
customThe phases were partitioned
washthe organic phase washed with H2O (1×500 mL), 1 M aq. HCl (2×500 mL), and brine (1×500 mL)
dry with materialThen, the organic phase was dried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by flash chromatography
washeluting with hexanes/EtOAc (3:2 gradient to 2:3)

Quellen und Nachweise

ORD-Eintrag: ord-24519959f36d43c2b0f64ebff7ccf4ee
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07390801B2

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