886-64-6

Usage

Chemical Properties

White crystalline powder

InChI:InChI=1/C11H14N2O3/c12-10(14)6-7-13-11(15)16-8-9-4-2-1-3-5-9/h1-5H,6-8H2,(H2,12,14)(H,13,15)

Upstream product

• 54755-77-0 N-benzyloxycarbonyl-3-aminopropionic acid methyl ester 
• 2304-94-1 3-(benzyloxycarbonylamino)propanoic acid 
• 82267-36-5 N-Cbz-beta-alanine ethyl carbonic anhydride 
• 543-27-1 isobutyl chloroformate 

Downstream Products

• 4726-85-6 β-alaninamide 
• 1200437-92-8 C₁₈H₁₈N₂O₃ 
• 1242584-18-4 phenyl[N-(R,S)-[N-benzyloxycarbonyl-β-alaninyl]-1-aminophenylmethyl]phosphinic acid 
• 59543-01-0 benzyloxycarbonyl-L-prolyl-β-alaninamide 
• 183444-82-8 {(S)-5-(2-Benzyloxycarbonylamino-ethylcarbamoyl)-5-[(S)-2-((R)-2-tert-butoxycarbonylamino-propionylamino)-3-phenyl-propionylamino]-pentyl}-carbamic acid tert-butyl ester 
• 183444-81-7 {(S)-5-(2-Benzyloxycarbonylamino-ethylcarbamoyl)-5-[(S)-2-((R)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-4-methyl-pentanoylamino]-pentyl}-carbamic acid tert-butyl ester 
• 77153-05-0 N¹-benzyloxycarbonyl-N²-t-butoxycarbonyl-1,2-ethanediamine 
• 72080-83-2 2-benzyloxycarbonylaminoethylamine 
• 18807-71-1 benzyl N-(2-aminoethyl)carbamate hydrochloride 

Relevant academic research and scientific papers

Direct synthesis of phosphinopeptides containing C-terminal α-aminoalkylphosphinic acids

A series of phosphinopeptides containing C-terminal α- aminoalkylphosphinic acids were prepared in good yields directly in one-pot reactions of 2-(N-benzoxycarbonylamino)alkanamides/peptide amides, aldehydes, and aryldichlorophosphines, followed by hydrolysis. In the current method, the peptide bond was formed in a Mannichtype reaction. Springer-Verlag 2010.

2-Phenyl-tetrahydropyrimidine-4(1H)-ones - Cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-β2-homoaspartate.

EPC-synthesis of β-amino acid derivatives through lithiated hydropyrimidines

Racemic and enantiopure 2-tert-butyltetrahydropyrimidinones (from pivalaldehyde and 3-aminocarboxylic acids) are converted to Alloc-, Boc-, and Z-protected cyclic imino esters (7-10, Schemes 2-4). These are deprotonated to Li enaminates (K, L). Reactions with electrophiles (prim., sec. alkyl, allyl, benzyl, propargyl halides, aldehydes, imines, enoates) give good yields and are highly diastereoselective (products 11-42, Schemes 5-10). A two-step cleavage (removal of protecting group and hydrolysis) under very mild conditions converts the heterocyclic products to α-branched β-amino acid methyl esters (43-61, Schemes 11-13). The structure of the products is determined by NMR spectroscopy (Figure 1), by chemical correlation (Scheme 14), and by X-ray analysis (Figure 2, 3, 7, Table 1). A structure of the Li enaminates is proposed (Figure 4). Mechanistic models are derived for the reactions occurring with formation of two stereogenic centers with relative topicity like (Figures 5, 6).

Design and synthesis of peptides passing through the blood-brain barrier

The blood-brain barrier (BBB) is a highly selective membranous barrier regulating the transport of substances in blood into the brain parenchyma. At present, delivery of biologically active peptides or peptide drugs into the brain is quite an important subject from the standpoint of chemotherapy for brain diseases H-MeTyr-Arg-MeArg-D-Leu-NH(CH2)8NH2 termed 001-C8 was first synthesized to elucidate the structural specificity of peptides for passing through the BBB. The Na-methylamino acid and D-amino acid residues were appropriately situated in this peptide to protect against the digestion by peptidase. Furthermore, a number of basic peptides were prepared as 001-C8 analogs for studying the relationship between structure and BBB permeability of peptides.

THE REACTION OF BENZENE WITH N-(BENZYLOXYCARBONYL)-1-AMINOCYCLOPROPANE-1-CARBOXAMIDE

The treatment of N-(benzyloxycarbonyl)-1-aminocyclopropane-1-carboxamide with benzene caused cleavage of the cyclopropane ring with the formation of a β-alaninamide derivative.

L-Pyroglutamyl-L-histidyl-L-prolyl-beta-alaninamide and salts

This disclosure relates to L-pyroglutamyl-L-histidyl-L-prolyl-beta-alaninamide and acid addition salts thereof as anti-depressant agents.