Development of the Hofmann rearrangement of Nα-tosylasparagine through calorimetric and NMR analysis

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9533-9534

  Amato, Joseph S ^a   Bagner, Carl ^a   Cvetovich, Raymond J ^a   Gomolka, Sue ^a   Hartner Jr , Frederick W ^a   Reamer, Robert ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARAGINE;

ARTICLE; CALORIMETRY; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0032509251     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980799l     Document Type: Article

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10. Mettler Instrument Co.
11. 5: C, 46.47; H, 4.25; S, 11.28; N, 9.85. Found: C, 46.16; H, 4.11; S, 11.30; N, 9.68. This intermediate was shown to proceed to product in NMR experiments consistent with the original NMR experiments.
12. The value of the heat of formation of 6 was estimated on the basis of the heat of formation of 3-aminopropionic acid (-138 kcal/ mol) plus the heat of formation of a secondary amine from hydrocarbon (-3.8 kcal/mol).