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Syntheses of [ 13 C, 15 N]‐labeled polyamines
Author(s) -
Hara Takeshi,
Xu Yong Ji,
Sasaki Hitomi,
Niitu Masaru,
Samejima Keijiro
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/1099-1344(200009)43:10<1005::aid-jlcr386>3.0.co;2-l
Subject(s) - chemistry , phthalimide , triphenylphosphine , tetrahydrofuran , yield (engineering) , derivative (finance) , spermidine , chloroform , potassium cyanide , halogenation , cyanide , potassium , organic chemistry , medicinal chemistry , catalysis , materials science , solvent , economics , financial economics , metallurgy , enzyme
[1,4‐ 13 C 2 ,1,4‐ 15 N 2 ]butanediamine ( 1 ), a key compound in the syntheses of [5,8‐ 13 C 2 ,1,4,8‐ 15 N 3 ]spermidine ( 2 ) and [5,8‐ 13 C 2 ,1,4,8,12‐ 15 N 4 ]spermine ( 3 ), has been prepared as part of a 6‐step process from 1,2‐dibromoethane using potassium [ 13 C]cyanide and potassium [ 15 N]phthalimide. In the course of the syntheses, it was found that 1,4‐dibromobutane was generated from tetrahydrofuran when bromination using triphenylphosphine and tetrabromomethane took place. A high yield preparation of monobenzyloxycarbonyl (Z) derivative of 1 , a precursor for 2 , was obtained using a water‐soluble Z agent, Z‐DSP, in a two‐phase system of alkaline solution and chloroform. All the steps for 1 , 2 , and 3 , were aimed at minimizing the loss of stable isotopes. Copyright © 2000 John Wiley & Sons, Ltd.