메뉴 건너뛰기




Volumn 49, Issue 41, 2008, Pages 6003-6006

Mono-acylation of symmetric diamines in the presence of water

Author keywords

Allyl carbonate protection; Boc protection; Diamine; Mono acylation

Indexed keywords

CARBONIC ACID; DIAMINE; ESTER; WATER;

EID: 50149101556     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.174     Document Type: Article
Times cited : (22)

References (22)
  • 12
    • 50149121446 scopus 로고    scopus 로고
    • The role of water in this mono-acylation reaction is unknown at this time. One hypothesis is that diamines form clusters through intermolecular hydrogen bonding in organic solvents like those formed by BuLi in hexane. This cluster formation lowers the reactivity of the diamine toward acylating agents. Compared to diamine, the mono-acylated product is associated with the clusters to a lesser degree and is therefore more reactive. As a result, di-acylated product is favored over mono-acylated product in organic media. In the presence of water, the clusters may be broken by hydrogen bonding between the diamine and water, and the reactivity of diamine is increased. This would lead to a 50% theoretical yield of mono-acylated product.
    • The role of water in this mono-acylation reaction is unknown at this time. One hypothesis is that diamines form clusters through intermolecular hydrogen bonding in organic solvents like those formed by BuLi in hexane. This cluster formation lowers the reactivity of the diamine toward acylating agents. Compared to diamine, the mono-acylated product is associated with the clusters to a lesser degree and is therefore more reactive. As a result, di-acylated product is favored over mono-acylated product in organic media. In the presence of water, the clusters may be broken by hydrogen bonding between the diamine and water, and the reactivity of diamine is increased. This would lead to a 50% theoretical yield of mono-acylated product. The higher than 50% yield may be attributed to the reduced reactivity of the second amino group in mono-acylated diamine caused by the electron-withdrawing amide group, lower solubility of mono-acylated diamine than diamine in the reaction media and the solid state of the mono-acylated product and the liquid state of diamine at the reaction temperature.
  • 19
    • 50149096485 scopus 로고    scopus 로고
    • Xie, Q.; Wenkert, D.; Shen, Y.; Vande Woude, G. F.; Hay, R. PCT Int. Appl. WO 2005095347, 2005;89 pp.
    • Xie, Q.; Wenkert, D.; Shen, Y.; Vande Woude, G. F.; Hay, R. PCT Int. Appl. WO 2005095347, 2005;89 pp.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.