613675-75-5

Basic information

• Product Name: tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate
• Synonyms: tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate
• CAS NO: 613675-75-5
• Molecular Weight: 278.351
• Mol File: 613675-75-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate(613675-75-5)
• EPA Substance Registry System: tert-butyl N-{[(2-phenylethyl)carbamoyl]methyl}carbamate(613675-75-5)

Safety Data

• Hazardous Substances Data: 613675-75-5(Hazardous Substances Data)

Upstream product

• 4530-20-5 BOC-glycine 
• 537710-06-8 N-Boc-glycine propargyl ester 
• 64-04-0 phenethylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 21639-02-1 N-p-nitrophenyloxycarbonylglycine 

Downstream Products

• 55677-60-6 α-amino-N-(2-phenylethyl)acetamide hydrochloride 
• 315249-56-0 (R)-5-Guanidino-2-phenylmethanesulfonylamino-pentanoic acid ({(S)-1-benzyl-2-hydroxy-2-[(phenethylcarbamoyl-methyl)-carbamoyl]-ethylcarbamoyl}-methyl)-methyl-amide 
• 749838-42-4 C₃₆H₄₇N₉O₉S 
• 190953-67-4 2-(2-phenylethylamino)ethylcarbamic acid tert-butyl ester 
• 62885-88-5 α-amino-N-(2-phenylethyl)acetamide 

Relevant articles and documents

Propargyl-Assisted Selective Amidation Applied in C-terminal Glycine Peptide Conjugation

Alkyl esters, such as propargyl esters, typically lack the electron-withdrawing inductive effects needed to participate in nucleophilic acyl substitution reactions. Herein, we report an unusual observation in which glycine propargyl ester derivatives displayed selective, base-independent reactivity towards linear alkylamines under mild, metal-free conditions. Through global reaction route mapping (GRRM) modeling calculations, it is predicted that these observations may be governed by factors related to hydrogen-bonding and intermolecular interactions, rather than electron-withdrawing inductive effects. Based on this concept of propargyl-assisted selective amidation, a direct application was made to develop a novel site-specific C-terminal glycine peptide bioconjugation technique as a proof-of-concept, which relies upon the selective reactivity of glycine propargyl esters over that of aspartate and glutamate side-chain-linked propargyl esters.

N,N′-disubstituted cinnamamide derivatives potentiate ciprofloxacin activity against overexpressing NorA efflux pump Staphylococcus aureus 1199B strains

A multi-step procedure has been described which afforded satisfactory yields of N,N′-disubstituted cinnamamides derived from N-Boc-protected amino acids (Boc-Gly, Boc-Val, Boc-Phe). The key step of this synthesis was a regioselective RedAl reduction of an

Sulfur incorporation generally improves Ricin inhibition in pterin-appended glycine-phenylalanine dipeptide mimics

Several 7-aminoamido-pterins were synthesized to evaluate the electronic and biochemical subtleties observed in the 'linker space' when N-{N-(pterin-7-yl)carbonylglycyl}-l-phenylalanine 1 was bound to the active site of RTA. The gylcine-phenylalanine dipeptide analogs included both amides and thioamides. Decarboxy gly-phe analog 2 showed a 6.4-fold decrease in potency (IC50 = 128 μM), yet the analogous thioamide 7 recovered the lost activity and performed similarly to the parent inhibitor (IC50 = 29 μM). Thiourea 12 exhibited an IC50 nearly six times lower than the oxo analog 13. All inhibitors showed the pterin head-group firmly bound in their X-ray structures yet the pendants were not fully resolved suggesting that all pendants are not firmly bound in the RTA linker space. Calculated log P values do not correlate to the increase in bioactivity suggesting other factors dominate.