A mild and general one-pot preparation of cyanoethyl-protected tetrazoles

Tetrahedron Letters

Volumn 51, Issue 15, 2010, Pages 2010-2013

  Kennedy, Lawrence J ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CHLORIDE; CYANOETHYL AMIDE; IMIDOYL CHLORIDE; NICOTINAMIDE; PHOSPHOROUS PENTACHLORIDE; PYRIDINE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPOPHILICITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ONE POT SYNTHESIS; REACTION ANALYSIS; SOLUBILITY; STEREOSPECIFICITY; TEMPERATURE;

EID: 77949304281     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.034     Document Type: Article

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16. Elevated temperature (40 °C) was found to be optimal, compared to reduced or ambient temperature, for complete conversion of the starting amide to the corresponding imidoyl chloride.
17. Addition of 1-2 equiv of azidotrimethylsilane typically resulted in incomplete tetrazole formation.
18. All amide-forming reactions were performed on a 1-2 mmol scale. All tetrazole-forming reactions were performed on a 0.5 mmol scale. Reaction conditions are not optimized.
19. - 281.1; found: 281.3.
20. 3): δ = 177.59, 124.95, 133.16, 128.94, 127.80, 117.88, 46.67, 35.86, 26.91, 18.00. LC-MS: m/z calcd for
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22. 5O
23. In an attempt to limit the potential formation of hydrazoic acid during work-up, the reactions were quenched with aqueous sodium bicarbonate. Throughout the course of this study it was found that a freshly prepared solution of sodium bicarbonate (pH ∼8) was optimal to work up the reactions. Sodium bicarbonate solution becomes more basic over time (to pH ∼10), which can lead to partial cleavage of the cyanoethyl-protecting group (5-10%).
24. Numerous unidentified species were observed via HPLC and LC-MS analysis.
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