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59279-60-6

  • Product NameN-Boc-L-Glutamic Acid dimethyl ester
  • Molecular FormulaC12H21NO6
  • Molecular Weight275.302
  • Purity99%
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Product Details

Quick Details

  • CasNo： 59279-60-6
  • Molecular Formula： C12H21NO6
  • Purity： 99%

High Quality N-Boc-L-Glutamic Acid dimethyl ester 59279-60-6 powder

  • Molecular Formula:C12H21NO6
  • Molecular Weight:275.302
  • Vapor Pressure:1.07E-05mmHg at 25°C 
  • Melting Point:43.0 to 47.0 °C 
  • Refractive Index:1.452 
  • Boiling Point:370.9 °C at 760 mmHg 
  • PKA:10.86±0.46(Predicted) 
  • Flash Point:178.1 °C 
  • PSA：90.93000 
  • Density:1.117g/cm3 
  • LogP:1.39680 

(R)-N-Boc-glutamic acid-1,5-dimethyl ester(Cas 59279-60-6) Usage

Uses

N-Boc-L-glutamic Acid 1,5-Dimethyl Ester is a useful research chemical. It can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development and chemical production processes. N-Boc-L-Glutamic Acid dimethyl ester is also used in the design of antiviral drug candidates targeting the SARS-CoV-2 main protease.
European Community (EC) Number 858-937-3
XLogP3-AA 1.1

Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)OC)C(=O)OC  

InChIKey: QNSPKWUAZQIIGZ-QMMMGPOBSA-N  

InChI: InChI=1S/C12H21NO6/c1-12(2,3)19-11(16)13-8(10(15)18-5)6-7-9(14)17-4/h8H,6-7H2,1-5H3,(H,13,16)/t8-/m0/s1  

59279-60-6 Relevant articles

An efficient synthesis of a key intermediate for the preparation of the rhinovirus protease inhibitor AG7088 via asymmetric dianionic cyanomethylation of N-Boc-l-(+)-glutamic acid dimethyl ester

Qingping Tian, Naresh K Nayyar, Srinivasan Babu, Lijian Chen, Junhua Tao, Steven Lee, Anthony Tibbetts, Terence Moran, Jason Liou, Ming Guo, Timothy P Kennedy

Tetrahedron Letters Volume 42, Issue 39, 24 September 2001, Pages 6807-6809

An efficient synthetic route to a key intermediate for the preparation of the rhinovirus protease inhibitor AG7088 has been developed employing a key asymmetric dianionic cyanomethylation of N-Boc-l-(+)-glutamic acid dimethyl ester. This methodology enables the preparation of this compound in kilogram quantities with an overall yield of 30%.

L-glutamic acid derivative and synthesis method and application thereof

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Paragraph 0044; 0048-0052; 0056; 00060-0064; 0066; 0070-0074, (2020/11/01)

The invention belongs to the technical f...

59279-60-6 Process route

dimethyl (2S)-2-{N-[(tert-butoxy)carbonyl]benzyloxycarbonylamino}pentane-1,5-dioate
500143-66-8

dimethyl (2S)-2-{N-[(tert-butoxy)carbonyl]benzyloxycarbonylamino}pentane-1,5-dioate

dimethyl (S)-N-(benzyloxycarbonyl)glutamate
67436-17-3

dimethyl (S)-N-(benzyloxycarbonyl)glutamate

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate
59279-60-6,130622-05-8,861658-15-3

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate

Conditions
Conditions Yield
With lithium bromide; In acetonitrile; at 65 ℃; for 10h;
 
With lithium bromide; In acetonitrile; at 65 ℃; for 10h; Title compound not separated from byproducts.;
 
di-<i>tert</i>-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-glutamic dimethyl ester hydrochloride
23150-65-4

L-glutamic dimethyl ester hydrochloride

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate
59279-60-6,130622-05-8,861658-15-3

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate

Conditions
Conditions Yield
With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 16h; Inert atmosphere;
100%
With iodine; at 20 ℃; for 1h;
88%
With zirconium(IV) chloride; In acetonitrile; at 20 ℃; for 0.166667h;
80%
With triethylamine; dmap; In dichloromethane; at 0 - 20 ℃;
68%
With triethylamine; In methanol; for 18h;
 
With sodium carbonate; In water; ethyl acetate; at 20 ℃; for 18h;
 
With dmap; triethylamine; In 1,4-dioxane; water;
 
With triethylamine; In methanol; for 6h; Cooling with ice;
 
With triethylamine; In dichloromethane; at 0 - 20 ℃; for 10.25h; Inert atmosphere;
 
With sodium hydroxide; In water; ethyl acetate; for 12h; pH=9 - 10; Large scale;
843 g

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