C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
530/5.06, 260/46
C07C 279/14 (2006.01) C07K 1/06 (2006.01) C07K 14/66 (2006.01)
Patent
CA 2006559
CASE 2976 NEW PROCESS FOR THE SYNTHESIS OF N.alpha.-FLUORENYLMETHOXYCARBONYL- N -TRITYL-ARGININE ABSTRACT An improvement is described in the synthesis method for N.alpha.-trityl- NG-trityl-arginine within a process for preparing N.alpha.-fluorenyl- methoxycarbonyl-NG-trityl-arginine from arginine, comprising: a) forming N.alpha.-trityl-NG-trityl-arginine b) selectively detaching the trityl group from the .alpha.-NH2 and c) introducing the fluorenylmethoxycarbonyl group in its place. The improvement consists of preparing the N.alpha.-trityl-NG-trityl- arginine by solubilizing the arginine in an aprotic organic solvent by tri-alkylsilylation both of the amino nitrogen and of the carboxyl group, followed by tritylation, with trityl chloride, of the .alpha.-amino nitrogen, and of the guanidino group after deprotonating this latter with a bicyclic guanidine. The new improved process can also lead to variable quantities of the arginine analogue di-tritylated at the guanidino group, namely N.alpha.-fluorenylmethoxycarbonyl-NG-di-trityl-arginine. This new compound, to which the present invention also relates, can also be used as such in peptide synthesis.
Caciagli Valerio
Verdini Antonio S.
Caciagli Valerio
Robic Robic & Associes/associates
Sclavo S.p.a.
Verdini Antonio S.
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