4976-88-9

Basic information

• Product Name: N-(tert-Butoxycarbonyl)-L-glutamine methyl ester
• Synonyms: N-(tert-Butoxycarbonyl)-L-glutamine methyl ester;N2-[(1,1-DiMethylethoxy)carbonyl]-L-glutaMine Methyl Ester;N2-Carboxy-glutaMine N-tert-Butyl Methyl Ester
• CAS NO: 4976-88-9
• Molecular Formula: C₁₁H₂₀N₂O₅
• Molecular Weight: 260.2869
• Product Categories: Amino Acids & Derivatives;Chiral Reagents
• Mol File: 4976-88-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 459.8±40.0 °C(Predicted)
• Appearance: /
• Density: 1.146±0.06 g/cm3(Predicted)
• Solubility: Chloroform, Methanol
• PKA: 11.04±0.46(Predicted)
• CAS DataBase Reference: N-(tert-Butoxycarbonyl)-L-glutamine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butoxycarbonyl)-L-glutamine methyl ester(4976-88-9)
• EPA Substance Registry System: N-(tert-Butoxycarbonyl)-L-glutamine methyl ester(4976-88-9)

Safety Data

• Hazardous Substances Data: 4976-88-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 67-56-1 methanol 
• 15387-45-8 Boc-Gln-ONp 

Relevant articles and documents

Kinetic resolution of esters via metal catalyzed methanolysis reactions

Some chiral lanthanide complexes of the Schiff base adducts of: a) bis(2-pyridylcarboxaldehyde) and (1R),(2R)-trans-1,2-diaminocyclohexane (Pyr-R,R′-chxn: 3); b) 6-methyl-2-pyridylcarboxaldehyde and (1R),(2R)-trans 1,2-diaminocyclohexane (MePyr-chxn, 4); and c) 2,6-pyridyldicarboxaldehyde and (1R),(2R)-trans-1,2-diaminocyclohexane ((Pyr-R,R′-chxn)2, 5) have been screened for their utility to promote kinetic resolution via metal catalyzed alcoholyses of the p-nitrophenyl esters of chiral d- and l-Boc-protected glutamine and phenylalanine. Solvents were varied to optimize the kinetic selectivity values, defined as k 2L/k2D or k2 D/k2L, for the methanolysis and in some cases, ethanolysis of these substrates. At ambient temperature the greatest selectivity was found for the ethanolysis of Boc-Gln-OPNP, catalyzed by 3:Yb 3+:(-OEt) (k2L/k2 D = 7.2). The greatest selectivity for Boc-Phe-OPNP is k 2D/k2L = 3.9 for its methanolysis promoted by 5:La3+:(-OMe). A kinetic method is introduced for the determination of both d and l rate constants for catalyzed alcoholysis from a single kinetic experiment. The activation parameters ΔH ? and ΔS? were determined for the metal catalyzed methanolysis and ethanolysis of the Boc-Gln-OPNP substrates, and selectivity factors were found to increase at lower temperatures. A low temperature time course for the ethanolysis of racemic Boc-Gln-OPNP catalyzed by 3:Yb3+:(-OEt) at -15 °C indicated that after 3 hours 60% residual d-enantiomer was observed having an enantiomeric excess of >95% ee. The activation parameters for the ethanolysis of the same substrate catalyzed by (Pyr-R,R′-chxn)2:La3+:(-OEt) predict a k2D/k2L = 40.4 at -40 °C with a large ee of >99% with ～80% of l isomer remaining at that temperature which has been experimentally confirmed. The Royal Society of Chemistry.