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Ethyl D-(-)-pyroglutamate, also known as (R)-(-)-5-Ethylcarboxyl-2-pyrrolidinone, is a waxy solid compound with the CAS number 68766-96-1. It is primarily utilized in the field of organic synthesis due to its unique chemical properties.

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  • 68766-96-1 Structure
  • Basic information

    1. Product Name: Ethyl D-(-)-pyroglutamate
    2. Synonyms: D-Pyroglutamic ethyl ester;(R)-5-Oxoproline ethyl ester, D-5-Oxo-2-pyrrolidinecarboxylic acid ethyl ester;(R)-5-Oxoproline ethyl ester, D-5-Oxo-2-pyrrolidinecarboxylic acid ethyl ester, D-Pyroglutamic acid ethyl ester, Ethyl 5-oxo-D-proline, Ethyl pyroglutamate;Ethyl D-(-)-pyroglutamate;(2R)-5-Oxo-2β-pyrrolidinecarboxylic acid ethyl ester;(R)-5-Oxo-2-pyrrolidinecarboxylic acid ethyl ester;Ethyl (R)-(-)-2-pyrrolidone-5-carboxylate,99%;Ethyl (R)-(-)-2-pyrrolidone-5-carboxylateD(-)-Pyroglutamic acid ethyl esterEthyl (R)-(-)-pyroglutamateEthyl D(-)-pyroglutamate
    3. CAS NO:68766-96-1
    4. Molecular Formula: C7H11NO3
    5. Molecular Weight: 157.17
    6. EINECS: N/A
    7. Product Categories: Chiral Reagents;Heterocycles;Miscellaneous Reagents
    8. Mol File: 68766-96-1.mol
  • Chemical Properties

    1. Melting Point: 53-57 °C
    2. Boiling Point: 176 °C12 mm Hg(lit.)
    3. Flash Point: >230 °F
    4. Appearance: waxy solid
    5. Density: 1.2483 (rough estimate)
    6. Vapor Pressure: 0.000519mmHg at 25°C
    7. Refractive Index: n20/D 1.478(lit.)
    8. Storage Temp.: 0-6°C
    9. Solubility: Chloroform (Slightly), Methanol (Slightly)
    10. PKA: 14.78±0.40(Predicted)
    11. BRN: 82622
    12. CAS DataBase Reference: Ethyl D-(-)-pyroglutamate(CAS DataBase Reference)
    13. NIST Chemistry Reference: Ethyl D-(-)-pyroglutamate(68766-96-1)
    14. EPA Substance Registry System: Ethyl D-(-)-pyroglutamate(68766-96-1)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 37/39-26
    4. WGK Germany: 3
    5. RTECS:
    6. F: 3-10
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 68766-96-1(Hazardous Substances Data)

68766-96-1 Usage

Uses

Used in Organic Synthesis:
Ethyl D-(-)-pyroglutamate is used as a synthetic building block for the creation of various organic compounds. Its unique structure and properties make it a valuable component in the synthesis of complex molecules, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl D-(-)-pyroglutamate is used as an intermediate in the synthesis of drugs. Its specific stereochemistry and functional groups enable the development of targeted therapeutic agents, potentially leading to more effective treatments for various medical conditions.
Used in Agrochemical Industry:
Ethyl D-(-)-pyroglutamate is also employed in the agrochemical industry as a precursor for the development of novel pesticides and other crop protection agents. Its unique properties allow for the creation of more selective and environmentally friendly products, contributing to sustainable agricultural practices.

Check Digit Verification of cas no

The CAS Registry Mumber 68766-96-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,8,7,6 and 6 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 68766-96:
(7*6)+(6*8)+(5*7)+(4*6)+(3*6)+(2*9)+(1*6)=191
191 % 10 = 1
So 68766-96-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m1/s1

68766-96-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Aldrich

  • (309788)  Ethyl(R)-(−)-2-pyrrolidone-5-carboxylate  98%

  • 68766-96-1

  • 309788-1G

  • 471.51CNY

  • Detail
  • Aldrich

  • (309788)  Ethyl(R)-(−)-2-pyrrolidone-5-carboxylate  98%

  • 68766-96-1

  • 309788-5G

  • 1,805.31CNY

  • Detail

68766-96-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl D-(-)-pyroglutamate

1.2 Other means of identification

Product number -
Other names ethyl (2R)-5-oxopyrrolidine-2-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:68766-96-1 SDS

68766-96-1Relevant articles and documents

Diastereoselective synthesis and biological evaluation of enantiomerically pure tricyclic indolines

He,Griffiths,Wang,Wang

supporting information, p. 4241 - 4245 (2017/07/10)

Tricyclic indolines are common in both natural products and synthetic chemical probes. In this study we demonstrated that enantiomerically pure tricyclic indolines can be prepared from an inexpensive commercially available chiral starting material, pyroglutamic acid. The synthesis features a highly diastereoselective gold-catalyzed cyclization of alkyne-tethered indoles and subsequent diastereoselective reductive ring-opening reaction. Using this approach, we synthesized analogs of our previously discovered tricyclic indoline probes that possess antibacterial and resistance-modifying activity. The biological activity against methicillin-resistant Staphylococcus aureus (MRSA) of these analogues was evaluated and reported. The synthetic approach reported may be leveraged in the future to prepare diastereopure chemical probes for the determination of biological targets for drug discovery.

CYCLIC AMINE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS

-

Paragraph 0410; 0411; 0412, (2015/03/31)

There is described a novel group of cyclic amine derivative compounds, having an EP4 receptor antagonistic activity and specifically pharmaceutical compounds which are useful for the treatment or alleviation of Prostaglandin E mediated diseases. The present invention therefore relates to novel compounds which are selective antagonists of the EP4 subtype of PGE2 receptors with analgesic and antinflammatory activity, processes for their preparation, pharmaceutical compositions containing them and their use as medicaments, inter alia for the treatment or alleviation of Prostaglandin E mediated diseases such as acute and chronic pain, osteoarthritis, inflammation-associated disorder as arthritis, rheumatoid arthritis, cancer, migraine and endometriosis.

PROCESS FOR THE SYNTHESIS OF SUBSTITUTED GAMMA LACTAMS

-

Paragraph 0049-0050, (2014/03/24)

The present invention provides synthetic processes for the preparation of a variety of well-defined substituted gamma lactams. The compounds that can be prepared by the process of the invention are useful for treating a variety of conditions. In some embodiments of the invention, the compounds are useful for treating ocular disorders, such as, for example, glaucoma, lowering of elevated intraocular pressure, and the like. In other embodiments, the compounds are useful for treating irritable bowel disease. In further embodiments, the compounds are useful in promoting hair growth. In still further embodiments, the compounds are useful in promoting wound healing, scar reduction, and the like.

PROCESS FOR THE SYNTHESIS OF SUBSTITUTED GAMMA LACTAMS

-

Page/Page column 11, (2014/03/25)

The present invention provides synthetic processes for the preparation of a variety of well-defined substituted gamma lactams. The compounds that can be prepared by the process of the invention are useful for treating a variety of conditions. In some embodiments of the invention, the compounds are useful for treating ocular disorders, such as, for example, glaucoma, lowering of elevated intraocular pressure, and the like. In other embodiments, the compounds are useful for treating irritable bowel disease. In further embodiments, the compounds are useful in promoting hair growth. In still further embodiments, the compounds are useful in promoting wound healing, scar reduction, and the like.

CYCLIC AMINE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS

-

Page/Page column 51; 52, (2013/03/26)

There is described a novel group of cyclic amine derivative compounds, having an EP4 receptor antagonistic activity and specifically pharmaceutical compounds which are useful for the treatment or alleviation of Prostaglandin E mediated diseases. The present invention therefore relates to novel compounds which are selective antagonists of the EP 4 sub type of PGE2 receptors with analgesic and antinflammatory activity, processes for their preparation, pharmaceutical compositions containing them and theiruse as medicaments, inter alia for the treatment or alleviation of Prostaglandin E mediated diseases such as acute and chronic pain, osteoarthritis, inflammation-associated disorder as arthritis, rheumatoid arthritis, cancer, migraine and endometriosis.

Discovery of a novel class of potent and orally bioavailable sphingosine 1-phosphate receptor 1 antagonists

Ibrahim, Mohamed A.,Johnson, Henry W. B.,Jeong, Joon Won,Lewis, Gary L.,Shi, Xian,Noguchi, Robin T.,Williams, Matthew,Leahy, James W.,Nuss, John M.,Woolfrey, John,Banica, Monica,Bentzien, Frauke,Chou, Yu-Chien,Gibson, Anna,Heald, Nathan,Lamb, Peter,Mattheakis, Larry,Matthews, David,Shipway, Aaron,Wu, Xiang,Zhang, Wentao,Zhou, Sihong,Shankar, Geetha

experimental part, p. 1368 - 1381 (2012/04/04)

A series of subtype selective sphingosine 1-phosphate receptor 1 (S1P 1) antagonists are disclosed. Our high-throughput screening campaign revealed hit 1 for which an increase in potency and mouse oral exposure was achieved with minor modifications to the chemical scaffold. In vivo efficacy revealed that at high doses compounds 12 and 15 inhibited tumor growth. Further optimization of our lead series led to the discovery of proline derivatives 37 (XL541) and 38 which had similar efficacy as our first generation analogues at significantly lower doses. Analogue 37 displayed excellent pharmacokinetics and oral exposure in multiple species.

Synthesis of 3-guaninyl- and 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone nucleosides

Saleh, Abdullah,D'Angelo, John G.,Morton, Martha D.,Quinn, Jesse,Redden, Kendra,Mielguz, Rafal W.,Pavlik, Christopher,Smith, Michael B.

scheme or table, p. 5574 - 5583 (2011/10/02)

l- And d-glutamic acids, as well as trans-4-hydroxy-l-proline, are converted to the corresponding 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analog. The protecting group used to block the lactam nitrogen in key intermediates has a significant effect on the diastereoselectivity of the coupling reaction with adenine or guanine.

PTERIDINONES AS INHIBITORS OF POLO - LIKE KINASE

-

Page/Page column 81, (2011/07/09)

The present invention provides compounds having a structure according to Formula (I) or a salt or solvate thereof, wherein ring A, X, R1, R2, R3, R4, R5 and R6, are defined herein. The invention further provides pharmaceutical compositions including the compounds of the invention and methods of making and using the compounds and compositions of the invention, e.g., in the treatment and prevention of various disorders, such as Parkinson's disease.

Synthesis and uses of pyroglutamic acid derivatives

-

Page/Page column 28, (2008/06/13)

Novel pyroglutamic acid derivatives (I), wherein R1 is -OH, -ORa, wherein Ra is alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, aralkyl or heterocyclyl; R2, R3 and R4 are independently H, a nitrogen protecting group which hydrolyzes under acidic conditions or phtalamide; X is a pharmaceutically acceptable anion; and Y is a N-containing group; either in the form of their isolated optically active stereoisomers or in the form of mixtures thereof, are useful compounds for enhancing an immuneresponse in a subject and/or for treating tumours, bacterial, fungal or viral infections, or autoimmune diseases.

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