60846-91-5

Basic information

• Product Name: (S)-3-N-CBZ-AMINO-SUCCINIMIDE
• Synonyms: (S)-benzyl 2,5-dioxopyrrolidin-3-ylcarbamate;Carbamic acid, [(3S)-2,5-dioxo-3-pyrrolidinyl]-, phenylmethyl ester (9CI)
• CAS NO: 60846-91-5
• Molecular Formula: C₁₂H₁₂N₂O₄
• Molecular Weight: 248.23
• Mol File: 60846-91-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 515.096 °C at 760 mmHg
• Flash Point: 265.321 °C
• Appearance: /
• Density: 1.354 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.79±0.50(Predicted)
• CAS DataBase Reference: (S)-3-N-CBZ-AMINO-SUCCINIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-N-CBZ-AMINO-SUCCINIMIDE(60846-91-5)
• EPA Substance Registry System: (S)-3-N-CBZ-AMINO-SUCCINIMIDE(60846-91-5)

Safety Data

• Hazardous Substances Data: 60846-91-5(Hazardous Substances Data)

Usage

General Description

(S)-3-N-CBZ-AMINO-SUCCINIMIDE is a chemical compound which often takes the form of a white or almost white crystalline powder. The "CBZ" in its name refers to 'carboxybenzyl', indicating that this compound is a derivative of a carboxybenzyl group. It’s typically used in pharmaceutical research, often in the process of creating innovative medicines. Generally, it is an important substance in medicinal chemistry due to its role in the peptide synthesis. This chemical is often synthesized in the laboratory and should be handled with proper safety measures due to its potentially reactive nature.

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

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

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 articles and documents

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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.

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