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Volumn 14, Issue 5, 2010, Pages 1177-1181

Amide bond formation via reversible, carboxylic acid-promoted lactone aminolysis

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ACIDS; AMIDE BOND; AMIDE BOND FORMATION; AMINOLYSIS; EQUILIBRIUM PROCESS;

EID: 77956936229     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op1001269     Document Type: Article
Times cited : (21)

References (28)
  • 14
    • 77956938295 scopus 로고    scopus 로고
    • 3, and 4-pyrrolopyridine
    • 3, and 4-pyrrolopyridine.
  • 17
    • 77956924815 scopus 로고    scopus 로고
    • 2O)
    • 2O).
  • 18
    • 77956903089 scopus 로고    scopus 로고
    • Increasing the amount of 6 to either 1.5 or 2 equiv did not significantly improve the reaction rate. Employing an excess of 6 with respect to amine 4 led to byproduct formation
    • Increasing the amount of 6 to either 1.5 or 2 equiv did not significantly improve the reaction rate. Employing an excess of 6 with respect to amine 4 led to byproduct formation
  • 19
    • 77956920329 scopus 로고    scopus 로고
    • The viscosity at 120 °C was determined to be 77 cP
    • The viscosity at 120 °C was determined to be 77 cP.
  • 20
    • 77956905060 scopus 로고    scopus 로고
    • We screened several sulfonic acids and mineral acids and found that, even for the acids that afforded soluble ammonium salts, the reaction rates were much slower, (+)-CSA, (-)-CSA, and (±)-CSA gave the best results but only reached 30% conversion after 2 h.
    • We screened several sulfonic acids and mineral acids and found that, even for the acids that afforded soluble ammonium salts, the reaction rates were much slower, (+)-CSA, (-)-CSA, and (±)-CSA gave the best results but only reached 30% conversion after 2 h.
  • 21
    • 77956905315 scopus 로고    scopus 로고
    • a values of the acids in the reaction medium are not known
    • a values of the acids in the reaction medium are not known.
  • 24
    • 77956907797 scopus 로고    scopus 로고
    • 3, OMe, Cl, and I) were not fully soluble in the reaction mixture, and the results are not included in Table 6.
    • 3, OMe, Cl, and I) were not fully soluble in the reaction mixture, and the results are not included in Table 6.
  • 25
    • 77956925111 scopus 로고    scopus 로고
    • The small, negative ρ value can also be thought of as a decrease in negative charge
    • The small, negative ρ value can also be thought of as a decrease in negative charge.
  • 26
    • 77956918105 scopus 로고    scopus 로고
    • No equilibrium isotope effect was observed. The rates using 2 with ND-Boc were the same as when the proteo compound was used
    • No equilibrium isotope effect was observed. The rates using 2 with ND-Boc were the same as when the proteo compound was used.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.