60846-91-5

Usage

Uses

Used in Pharmaceutical Research:
(S)-3-N-CBZ-AMINO-SUCCINIMIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its carboxybenzyl group provides a protecting function for the amino group during the synthesis process, which is crucial for the development of innovative medicines.
Used in Peptide Synthesis:
In the field of peptide synthesis, (S)-3-N-CBZ-AMINO-SUCCINIMIDE serves as a building block for the creation of peptide chains. The carboxybenzyl protecting group allows for the stepwise assembly of peptides, facilitating the synthesis of complex peptide structures with greater ease and precision.
Used in Medicinal Chemistry:
(S)-3-N-CBZ-AMINO-SUCCINIMIDE is utilized as a reagent in medicinal chemistry for the preparation of various bioactive compounds. Its unique properties enable the synthesis of molecules with specific biological activities, contributing to the discovery of new therapeutic agents.
Used in Laboratory Synthesis:
(S)-3-N-CBZ-AMINO-SUCCINIMIDE is often synthesized in laboratories for research purposes, where it is employed in the development of new synthetic routes and methodologies. Its synthesis and subsequent use in various chemical reactions provide valuable insights into the reactivity and potential applications of related compounds.

InChI:InChI=1/C12H12N2O4/c15-10-6-9(11(16)14-10)13-12(17)18-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,17)(H,14,15,16)/t9-/m0/s1

Upstream product

• 501-53-1 benzyl chloroformate 
• 4668-37-5 N-(benzyloxycarbonyl)asparagine methyl ester 
• 71-36-3 butan-1-ol 

Downstream Products

• 132920-84-4 (3S)-3-(methylamino)pyrrolidine dihydrochloride 
• 124166-11-6 (S)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester 
• 93185-73-0 N-(benzyloxycarbonyl)-L-asparaginamide 

Relevant academic research and scientific papers

Transesterification of α-amino esters catalyzed by a tetranuclear zinc cluster: Zn4(OCOCF3)6O

Transesterification of amino acid ester derivatives was developed using a tetranuclear zinc cluster, Zn4(OCOCF3)6O, as the catalyst. Because the reaction conditions were very mild, a variety of N-protective groups and functional groups on side chains were tolerated. Georg Thieme Verlag Stuttgart. New York.

Co-ordination chemistry of 3S-aminopyrrolidine and 3S-(methyl-amino)pyrrolidine: Crystallisation of the two diastereomers of dichloro[3S-(R,S-methylamino)pyrrolidine]palladium(II)

Complexes of divalent Cu, Ni, Pd and Pt with 3S-aminopyrrolidine (S-ap) have been prepared and characterised by a combination of NMR, CD, electronic, IR and microanalytical techniques. The chosen chirality of the stereogenic carbon (S) forces the secondary nitrogen to adopt the R stereochemistry on co-ordination with the conformation of the 5-membered chelate being λ. The planar [M(S-ap)2]2+ complexes exist as a mixture of cis and trans isomers in the solid state and in solution. The trans arrangement is forced upon co-ordination of an axial donor (X = halide, thiocyanate or nitrite) in the five-co-ordinate ions [Cu(S-ap)2X]+. Methylation of the primary amine of S-ap generates another secondary nitrogen centre in the new ligand 3S-(methylamino)pyrrolidine, S-meap. This exocyclic nitrogen is not restricted to a single configuration on co-ordination. The complexes [M(S-meap)Cl2], where M = Pd or Pt, have been prepared and characterised. Both diastereoisomers (R- and S-NMe) of [Pd(S-meap)Cl2] crystallise from aqueous solution as distinct crystal forms which can be separated by mechanical means. The structure of the NMe(R) isomer has been determined by X-ray crystallography.

Regioselective reductions of various 3-aminosuccinimides; application to the synthesis of two heterocyclic systems

The synthesis of novel pyrrolo[3,2-c]isoquinolines is investigated starting from 3-aminosuccinimides. Various known routes leading to 3-aminosuccinimides were tested but a new approach via nucleophilic addition of arylalkylamines on maleimide gave better results. The regioselectivity of the reduction of these compounds was shown to depend on the degree of substitution of the concerned 3-aminosuccinimide. The hydroxylactams are formed in-situ, then converted into the ethoxylactams. The latter, after generation of an iminium salt, afforded the target pyrroloisoquinolines and two further derivatives of another new heterocyclic system: the 3,6-methano-2,5-benzodiazocine.

Handy access to chiral N,N'-disubstituted 3-aminopyrrolidines

A new and rapid synthesis of (S)-3-aminopyrrolidines Z is proposed from N-protected (S)-Asparagine. Basic cyclization of methyl N-Z-(S)-Asparaginate 1 followed by one-pot N-benzylation directly leads to (S)-aminosuccinimide 3 which, after cleavage of the

Cyclo-(L-asparagyl-L-asparagyl) : Preparation and Crystal Structure

Two methods are described for the preparation of optically pure cyclo-(L-asparagyl-L-asparagyl) : (i) by self-condensation of (S)-3-aminopyrrolidine-2,5-dione in refluxing acetonitrile, and (ii) by self-co