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6211-16-1

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Highly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation
By employing a rhodium-Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.
Ji, Jianjian,Chen, Caiyou,Cai, Jiayu,Wang, Xinrui,Zhang, Kai,Shi, Liyang,Lv, Hui,Zhang, Xumu
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p. 7624 - 7627
(2015/07/15)

Highly enantioselective Michael reactions catalyzed by a chiral quaternary ammonium salt. Illustration by asymmetric syntheses of (S)-ornithine and chiral 2-cyclohexenones.
[formula: see text] The use of the chiral quaternary ammonium salts 1a and 1b makes possible enantioselective Michael reactions which have been applied to the asymmetric syntheses of (S)-ornithine (2) and the chiral 2-cyclohexenone 6.
Zhang,Corey
p. 1097 - 1100
(2007/10/03)

Aminosaeuren, I. Darstellung von Aminosaeuren aus Halogencarbonsaeure-alkylestern mit Alkalimetallcyanaten
α- and ω-halo- as well as α,ω-dihalocarboxylic alkyl esters react with potassium cyanate in the presence of alcohol at 80 - 120 deg C in dipolar aprotic solvents to yield α- and ω-(alkoxycarbonylamino)- and α,ω-bis(alkoxycarbonylamino)carboxylic alkyl esters, respectively, in good yields.Hydrolytic cleavage of these mono- or diurethanes with an aqueous solution of hydrochloric acid/formic acid leads to the corresponding amino acid hydrochlorides in nearly quantitative yields.
Effenberger, Franz,Drauz, Karlheinz,Foerster, Siegfried,Mueller, Wolfgang
p. 173 - 189
(2007/10/02)

Process for the production of aminoacid hydrochlorides/or diaminoacid dihydrochlorides
Aminoacid hydrochlorides or diaminoacid dihydrochlorides are produced by first reacting a halocarboxylic acid ester with an alkali metal cyanate in the presence of an alcohol to form the corresponding mono- or diurethane and then saponifying this to the corresponding mono- or dihydrochloride. The new process is relatively versatile in its use and above all opens up an elegant synthesis route for lysine.
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(2008/06/13)

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Chemical Properties

Melting Point: 197-199 °C (dec.)
Boiling Point: 308.7 °C at 760 mmHg
Flash Point:140.5 °C
Storage Temp.:Inert atmosphere,Room Temperature
Vapor Pressure: 0.00015mmHg at 25°C
Refractive Index: 18 ° (C=5, H2O)
Merck: 14,6874
BRN: 4538819
PSA: 89.34000
LogP: 2.14180

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