4931-66-2

  • Product NameL-Pyroglutamic Acid Methyl Ester
  • Molecular FormulaC6H9NO3
  • Molecular Weight143.142
  • Purity99%
  • AppearanceBrown oil
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Product Details

Quick Details

  • CasNo: 4931-66-2
  • Molecular Formula: C6H9NO3
  • Appearance: Brown oil
  • Purity: 99%

High Quality Chinese Factory Supply L-Pyroglutamic Acid Methyl Ester 4931-66-2

  • Molecular Formula:C6H9NO3
  • Molecular Weight:143.142
  • Appearance/Colour:Brown oil 
  • Vapor Pressure:3.64E-09mmHg at 25°C 
  • Refractive Index:1.486 
  • Boiling Point:304.7 °C at 760 mmHg 
  • PKA:14.65±0.40(Predicted) 
  • Flash Point:138.1 °C 
  • PSA:55.40000 
  • Density:1.204 g/cm3 
  • LogP:-0.23320 

Methyl L-pyroglutamate(Cas 4931-66-2) Usage

Chemical Properties

Brown Oil

Uses

Methyl (S)-Pyroglutamate (cas# 4931-66-2) is a compound useful in organic synthesis.

InChI:InChI=1/C17H14F3N3S2/c1-21-16(23-15-4-2-3-13(9-15)17(18,19)20)25-10-12-5-7-14(8-6-12)22-11-24/h2-9H,10H2,1H3,(H,21,23)

4931-66-2 Relevant articles

Synthesis of chiral 5-substituted 2-pyrrolidinones: An unusual one-step transformation

Wei, Zhong-Yong,Knaus, Edward E.

, p. 4439 - 4442 (1993)

An efficient methodology for the enantio...

Biotransformation of Licochalcone A by transgenic crown galls of Panax quinquefolium

Li, Jiayuan,Li, Ning,Huang, Bing,Zhao, Weihong,Wang, Wenli,Si, Yingying,Yan, Chunyan

, p. 72 - 76 (2014)

Licochalcone A, as main constituent of C...

A catalytic one-step process for the chemo- and regioselective acylation of monosaccharides

Kawabata, Takeo,Muramatsu, Wataru,Nishio, Tadashi,Shibata, Takeshi,Schedel, Hartmut

, p. 12890 - 12895 (2007)

An organocatalytic method for the chemo-...

-

Rapoport et al.

, p. 883 (1964)

-

Studies on pyrrolidinones: Some attempts to improve the synthesis of methyl N-(3,4,4′,5-tetramethoxybenzhydryl)pyroglutamate (HEI 81) by using N-acyl iminium salts methodologies

Bourry, Anne,Pitard, Franck,Rigo, Benoit,Sanz, Gerard,Camus, Fabrice,Norberg, Bernadette,Durant, Francois,Couturier, Daniel

, p. 109 - 118 (2002)

Some ways to use the N-acyl iminium salt...

Revised Structure of Anthelvencin A and Characterization of the Anthelvencin Biosynthetic Gene Cluster

Aubry, Céline,Clerici, Paolo,Gerbaud, Claude,Lautru, Sylvie,Micouin, Laurent,Pernodet, Jean-Luc

, p. 945 - 951 (2020)

Anthelvencins A and B are pyrrolamide me...

Design, synthesis and evaluation of hydrazine and acyl hydrazone derivatives of 5-pyrrolidin-2-one as antifungal agents

Billamboz, Muriel,Dascalu, Anca-Elena,Fayeulle, Antoine,Furman, Christophe,Ghinet, Alina,Lipka, Emmanuelle,Rigo, Beno?t

, (2020)

Twenty-eight 5-pyrrolidine-2-ones decora...

Enantioselective N-heterocyclic carbene-catalysed intermolecular crossed benzoin condensations: Improved catalyst design and the role of in situ racemisation

Delany, Eoghan G.,Connon, Stephen J.

supporting information, p. 248 - 258 (2021/01/14)

The enantioselective intermolecular cros...

Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis

Kim, Minje,Liu, Hung-wen,Ren, Daan,Wang, Shao-An

supporting information, p. 17148 - 17154 (2021/06/28)

Showdomycin is a C-nucleoside bearing an...

Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry

Sanchez, Clément A.,Gadais, Charlène,Chaume, Grégory,Girard, Sylvaine,Chelain, Evelyne,Brigaud, Thierry

supporting information, p. 382 - 387 (2021/01/13)

The straightforward synthesis of enantio...

Discovery of SY-5609: A Selective, Noncovalent Inhibitor of CDK7

Alnemy, Sydney,Bradley, Michael J.,Chuaqui, Claudio,Ciblat, Stephane,Hamman, Kristin B.,Hu, Shanhu,Kabro, Anzhelika,Ke, Nan,Malojcic, Goran,Marineau, Jason J.,Mihalich, Janessa,Roy, Stephanie,Savinainen, Anneli,Schmidt, Darby,Waters, Nigel J.,Whitmore, Kenneth Matthew,Wilsily, Ashraf,Winter, Dana K.,Zahler, Robert

, (2021/11/18)

CDK7 has emerged as an exciting target i...

4931-66-2 Process route

methanol
67-56-1

methanol

L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

methyl (S)-pyroglutamate
4931-66-2

methyl (S)-pyroglutamate

Conditions
Conditions Yield
With thionyl chloride; at 0 - 25 ℃;
100%
With methanesulfonic acid; In chloroform; water; Reflux;
100%
With Dowex-50W (X8-200) resin; Inert atmosphere; Reflux;
100%
With thionyl chloride; for 0.5h; Heating;
99.3%
With Amberlyst 15 resin; for 24h; Heating;
99%
With Dowex ion-exchange resin;
98%
With Dowex 50 W X 8; for 4h; Heating;
97%
With Amberlyst 15 wet resin; for 24h; Reflux;
97%
With Dowex; for 16h; Heating;
96%
With Dowex 50W X 8; Heating;
95%
With thionyl chloride; at 20 ℃; for 48h;
95%
With thionyl chloride; Ambient temperature;
94%
With thionyl chloride; at -5 - 20 ℃; for 10h;
94%
With thionyl chloride; at 20 ℃; for 12h;
94%
With thionyl chloride; for 3h; Ambient temperature;
93%
With Amberlyst 15; Reflux;
93%
With thionyl chloride;
92%
With thionyl chloride; at 0 - 20 ℃; Inert atmosphere;
92%
With thionyl chloride; at 20 ℃; for 24h;
92%
With thionyl chloride; In N,N-dimethyl-formamide; for 26h; Ambient temperature;
91%
With thionyl chloride; N,N-dimethyl-formamide; for 24h; Ambient temperature;
91%
With thionyl chloride;
91%
With toluene-4-sulfonic acid; for 12h; Heating;
90%
With thionyl chloride; at 0 - 20 ℃; for 4h; Inert atmosphere; Schlenk technique;
90%
With thionyl chloride; at 0 - 20 ℃; for 3h;
90%
With thionyl chloride; for 1.5h; Ambient temperature;
89.1%
With thionyl chloride; at 20 ℃; for 24h;
85%
With thionyl chloride; In toluene; at -15 - 20 ℃; Inert atmosphere;
83%
With thionyl chloride; for 72h;
81%
With thionyl chloride; at -15 - 20 ℃; Inert atmosphere;
81%
With thionyl chloride; at 20 ℃; for 16h; Inert atmosphere;
81%
With thionyl chloride; at -18 - 20 ℃;
81%
With thionyl chloride; for 2h; Ambient temperature;
80%
With thionyl chloride; for 24h; Ambient temperature;
80%
With thionyl chloride; at 20 ℃; for 3h; pH=0;
80%
With thionyl chloride; at 20 ℃;
80%
With thionyl chloride; at 20 ℃; for 14h;
79%
With thionyl chloride; for 1.5h; Heating;
76%
With thionyl chloride; at 20 ℃; Cooling with ice;
72%
With thionyl chloride; at 20 ℃; for 2h;
70%
With thionyl chloride; at 0 - 20 ℃;
70%
With thionyl chloride; at 0 - 20 ℃;
70%
With thionyl chloride; at 0 ℃; for 0.5h;
67%
With thionyl chloride; at 0 - 20 ℃; for 3h;
67.6%
With thionyl chloride; at 0 - 20 ℃; for 3h; Inert atmosphere; Sealed tube;
67.6%
With thionyl chloride; at 0 - 20 ℃; for 3h;
67.6%
With thionyl chloride; at 0 - 20 ℃; for 3h;
67.6%
With thionyl chloride; at 0 - 20 ℃; for 3h;
67.6%
With thionyl chloride; at 0 - 20 ℃; for 3h;
67.6%
With thionyl chloride; at 0 - 20 ℃; for 3h;
67.6%
With thionyl chloride; at 0 - 20 ℃; for 3h;
67.6%
With thionyl chloride; at 0 - 40 ℃;
58%
sulfuric acid; In benzene; Heating;
sulfuric acid; In benzene; for 20h; Heating;
With thionyl chloride;
With thionyl chloride; for 2h; Ambient temperature;
With Dowex 50WX2-200; for 3h; Heating;
With thionyl chloride; at 20 ℃; for 48h;
27.70 g
With thionyl chloride; at -20 - 20 ℃;
With thionyl chloride; at -15 - 20 ℃;
With thionyl chloride; at 0 - 20 ℃;
With thionyl chloride; at -15 ℃; for 2h;
With thionyl chloride; at -15 - 20 ℃; for 2.5h;
With hydrogenchloride; at 20 ℃; for 21h;
With thionyl chloride; at 10 - 30 ℃; for 2.08333h;
With thionyl chloride; at 10 - 30 ℃; for 2.08333h;
With thionyl chloride; at 0 - 23 ℃; for 12h;
With Dowex-H+; Heating / reflux;
With thionyl chloride;
With thionyl chloride; at -15 - 20 ℃;
With thionyl chloride; at 20 ℃;
With thionyl chloride; In methanol; at 0 - 20 ℃; for 2h;
With hydrogenchloride; In water; at 20 ℃; for 24h;
With toluene-4-sulfonic acid; for 24h; Reflux;
With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;
With thionyl chloride; at -5 - 30 ℃;
With thionyl chloride; at 20 ℃; Cooling with ice; Inert atmosphere;
With thionyl chloride; at 20 ℃; for 1h;
With thionyl chloride;
With thionyl chloride; at 0 - 18 ℃; for 1h;
With toluene-4-sulfonic acid; for 30h; Reflux;
3.161 g
With thionyl chloride; at 20 ℃; for 1h; Inert atmosphere;
L-Pyroglutamic acid
98-79-3

L-Pyroglutamic acid

methyl (S)-pyroglutamate
4931-66-2

methyl (S)-pyroglutamate

Conditions
Conditions Yield
With sulfuryl dichloride; sodium carbonate; In methanol; ethyl acetate;
92.8%
With sulfuryl dichloride; sodium carbonate; In methanol; ethyl acetate;
92.8%
With sulfuryl dichloride; sodium carbonate; In methanol; water; ethyl acetate; N,N-dimethyl-formamide;
91%
With sulfuryl dichloride; sodium carbonate; In methanol; water; ethyl acetate; N,N-dimethyl-formamide;
91%
Multi-step reaction with 2 steps
1: SOCl2
With thionyl chloride;
Multi-step reaction with 3 steps
1: 100 percent / saccharin / 2.5 h / Heating
2: 100 percent Chromat. / oxalyl chloride / CH2Cl2 / Heating
3: 86 percent / CH2Cl2 / 0.08 h / Heating
With oxalyl dichloride; saccharin; In dichloromethane;
With thionyl chloride; potassium carbonate; In methanol; water; ethyl acetate;
With thionyl chloride; In methanol; at 0 - 20 ℃; for 3.5h;

4931-66-2 Upstream products

  • 67-56-1
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    methanol

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    pyroglutamoyl chloride

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    dimethyl N-benzylideneglutamate

4931-66-2 Downstream products

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    methyl methylene bis-pyroglutamate

;

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