67729-36-6

Basic information

• Product Name: C₉H₁₁NO₂C₅H₈O₂CO₂C₄H₈
• CAS NO: 67729-36-6
• Molecular Weight: 365.426
• Mol File: 67729-36-6.mol
• Article Data: 62

Chemical Properties

• CAS DataBase Reference: C₉H₁₁NO₂C₅H₈O₂CO₂C₄H₈(CAS DataBase Reference)
• NIST Chemistry Reference: C₉H₁₁NO₂C₅H₈O₂CO₂C₄H₈(67729-36-6)
• EPA Substance Registry System: C₉H₁₁NO₂C₅H₈O₂CO₂C₄H₈(67729-36-6)

Safety Data

• Hazardous Substances Data: 67729-36-6(Hazardous Substances Data)

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 543-27-1 isobutyl chloroformate 
• 18942-49-9 Boc-D-Phe-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 63-91-2 L-phenylalanine 

Downstream Products

• 33662-25-8 (S)-N-Boc-phenylalanine benzylamide 
• 115313-19-4 1-diazo-3(R)-<<(1,1-dimethylethoxy)carbonyl>amino>-4-phenyl-2-butanone 
• 185543-01-5 (S)-3-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-chloro-4-oxo-pentanoic acid benzyl ester 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 138772-65-3 tert-butyl ((2S)-1-(((2S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 68835-84-7 L-phenylalanyl-L-leucine methyl ester trifluoroacetate 
• 83671-02-7 L-phenylalanyl-L-phenylalanine ethyl ester trifluoroacetate 
• 83588-10-7 L-Phe-D-Leu-OCH₃ trifluoroacetate 
• 385438-91-5 N-Boc-D-phenylalanine 2-amino-5-nitroanilide 
• 343310-59-8 ethyl N-(7-tert-butyloxycarbonyl-L-phenylalanylamido)-4-coumarinyl-acetate 
• 254100-49-7 [(S)-1-((S)-2-Methyl-1-thiazol-2-yl-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 214826-41-2 Boc-Phe-Orn(Z)-CH₂Cl 
• 52780-89-9 Boc-Phe-Lys(Z)-CH₂Cl 
• 40290-63-9 Methyl ester of N-t-butyloxycarbonyl-L-phenylalanyl-L-methionine 

Relevant articles and documents

C12 helices in long hybrid (αγ)n peptides composed entirely of unconstrained residues with proteinogenic side chains

Unconstrained γ4 amino acid residues derived by homologation of proteinogenic amino acids facilitate helical folding in hybrid (αγ)n sequences. The C12 helical conformation for the decapeptide, Boc-[Leu-γ4(R)Val

Process for the preparation of ibodutant (MEN15596) and related intermediates

This invention relates to a novel process for synthesizing the product ibodutant shown in the figure below, consisting of a small number of high-yield steps involving reagents and solvents with low environmental impact, characterized by the coupling of two portions, compounds (3) and (4), one of which (3) is synthesized by coupling of 6-methyl-2-benzo[b]thiophenecarboxylic acid (1) with 1-amino-alpha-alpha-cyclopentan carboxylic acid and subsequent cyclization with oxazolone, while the other, compound (4), is obtained from suitable highly selective functionalizations of 4-aminomethylpiperidine (2).

Sodium borohydride reduction of carbamoyl azide function: A synthesis of N-protected N'-formyl-gem-diaminoalkyl derivatives

A simple, efficient two-step synthesis of N-protected N′-formyl-gem- diaminoalkyl derivatives is reported. The procedure involves the unprecedented reduction of the carbamoyl azide of α-N-Boc/Fmoc/Z-protected amino acids and dipeptides (Boc = tert-butoxycarbonyl, Fmoc = 9-fluorenylmethoxycarbonyl, Z = benzyloxycarbonyl) by treatment with NaBH4 at room temperature. The reaction proceeds rapidly (45 min) without detectable epimerization (by HPLC-ESI-MS analysis) and is not influenced by the nature of the starting carbamoyl azide. The 1H and 13C NMR analyses of the synthesized N-protected N′-formamides were carried out in [D 6]DMSO. The spectra exhibited the presence of two rotameric forms in solution as a result of the restricted rotation around the N-CO formyl bond. The integration of the N-CH-N protons of the two isomers showed that the cis isomer (rotamer B) was the more abundant conformer by 60 to 78 %. The reported synthesis represents the potential value of carbamoyl azides as versatile chiral starting materials for many synthetic purposes. A simple two-step synthesis of N-protected N′-formyl-gem-diaminoalkyl derivatives is reported that employs the reduction of the carbamoyl azide of N-protected amino acids and N-protected dipeptide acids with NaBH4. This racemization-free protocol is compatible with the most commonly used N-protecting groups. Copyright