Dimethylformamide → 2-(Trimethylsilyl)ethyl 3-[cyclopropyl(4-ethoxy-4-oxobutyl)sulfamoyl]benzoate

HRID 1025426Notes

Reaction equation

[CH:1]1([NH:4][S:5]([C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=2)[C:11]([O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[O:12])(=[O:7])=[O:6])[CH2:3][CH2:2]1.Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:1]1([N:4]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[S:5]([C:8]2[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=2)[C:11]([O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:18])[CH3:19])=[O:12])(=[O:7])=[O:6])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2.12 g of 2-(trimethylsilyl)ethyl 3-(cyclopropylsulfamoyl)benzoate, 1.45 g of ethyl 4-bromobutyrate, 2.57 g of potassium carbonate, and 21 mL of DMF was stirred at 80° C. overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 2.48 g of 2-(trimethylsilyl)ethyl 3-[cyclopropyl(4-ethoxy-4-oxobutyl)sulfamoyl]benzoate as a colorless oily substance. ESI+: 456

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water and saturated brine in this order
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-6bf468a48dd04aa49424f7648e7f56cd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729068B2

Reaction notes

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