Preparation of optical active aliphatic a-amino acid
from fatty acid: synthesis of
Chao Qian Æ Ling Gong Æ Xin Zhi Chen
Received: 7 September 2007 / Accepted: 11 June 2008 / Published online: 8 January 2009
Ó Springer Science+Business Media B.V. 2009
Abstract A new synthesis of
-norvaline is described. Using valeric acid as the
raw material, a-brominevaleryl chloride was achieved by acyl chlorination and
a-position bromination in one-pot with the yield of 84.7%. The yields of the fol-
lowing ammoniation of a-brominevaleryl chloride and resolution of
were 88.7% and 26.7%, respectively.
-Norvaline was also obtained in a similar
method from the waste resolution solution. Other optical active amino acids, valine,
a-aminobutyric acid and alanine were also synthesized in similar ways.
Keywords Valeric acid Á
-Norvaline Á Resolution Á
Norvaline is a non-natural a-amino acid; its two optical isomers are of high
appliance value in the medicinal synthesis.
-Norvaline is the important interme-
diate of the preparation of Perindopril, which is a non-thiohydroxy ACE inhibitor
and used for the treatment of hyperpiesia and congestive heart failure with high
-Norvaline can be used as the chiral source to prepare some chiral
macrolides directionally, such as Pamamycin-607  and Epilachnene [5, 6].
Optical active norvaline canld be prepared from a biologic enzyme method or a
chemical method [7–11]. The biologic enzyme method did not ﬁt industrial
production for high cost and low yield, and no reporting interiorly. The conventional
chemical preparation method of
-norvaline is the Strecker synthesis, which used
cyanide and is therefore not the best choice. There has been little reporting about the
C. Qian Á L. Gong Á X. Z. Chen (&)
College of Materials Science and Chemical Engineering, Zhejiang University,
Hangzhou 310027, People’s Republic of China
Res Chem Intermed (2009) 35:117–121