Amide bond formation from selenocarboxylates and aromatic azides

Tetrahedron Letters

Volumn 46, Issue 48, 2005, Pages 8401-8405

  Wu, Xinghua ^a   Hu, Longqin ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Amidation; Aromatic azides; Selenocarboxylates

Indexed keywords

AMIDE; AROMATIC COMPOUND; AZIDE; CARBOXYLIC ACID DERIVATIVE; POTASSIUM; POTASSIUM DERIVATIVE; POTASSIUM METHOXIDE; SELENIDE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON; ROOM TEMPERATURE;

EID: 27644532678     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.145     Document Type: Article

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19. General procedure: To a solution of diacyl selenide (2.0 mmol) in EtOAc (20 mL) was added a suspension of KOMe (2.0 mmol) in DMSO (20 mL) at 5°C under nitrogen atmosphere. The resulting mixture was stirred at 5°C for 10 min. Then, the starting azide (1.0 mmol) was added into the above mixture. The reaction was allowed to gradually warm to room temperature. The reaction mixture was poured into ice water when TLC showed the disappearance of the starting azide or no further change of the reaction mixture. The black selenium powder was removed by filtration. The filtrate was extracted with EtOAc. After removal of solvents, the crude product was purified by flash column chromatography.
20. Stability measurement: The stability of benzeneselenocarboxylate 10 in DMSO/EtOAc (1:1) at room temperature was measured by monitoring the product formation between benzeneselenocarboxylate 10 and 4-nitrophenyl azide 12 under the above general reaction conditions. The reaction between benzeneselenocarboxylate 10 and 4-nitrophenyl azide 12 to form the product amide 24 was complete in less than 5 min (data not shown). Such fast product formation allows for the accurate measurement of the amount of benzeneselenocarboxylate 10 remained in solution during our stability study. Briefly, aliquots of freshly prepared benzeneselenocarboxylate 10 in DMSO/EtOAc (1:1) were incubated at room temperature and the amount of benzeneselenocarboxylate 10 was measured at different time intervals by the reaction with 2 equiv of 4-nitrophenyl azide (12 ) for at least 1 h. The reaction mixtures were separated on a Chromolith SpeedROD RP-18e column (50 x 4.6 mm) at 1 mL/min with a 10-min gradient of 10-90% acetonitrile containing 0.1% formic acid on a Shimadzu 2010 LCMS system. The N-(4-nitrophenyl) benzamide product 24 was quantitated based on UV absorption at 220 nm, and its structure was confirmed by the mass spectrometry detector. The peak area of N-(4-nitrophenyl) benzamide product 24 represents the amount of benzeneselenocarboxylate 10 that remained at a given time point and was plotted against the time of incubation. The data was fitted to a single, two parameter exponential decay equation in SigmaPlot to obtain the first-order rate constant.