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1-CBZ-4(R)-Hydroxypyrrolidine-2-carboxylic acid ethyl ester, with the molecular formula C14H19NO4, is a chemical compound that serves as an ethyl ester derivative of 1-CBZ-4(R)-Hydroxypyrrolidine-2-carboxylic acid. It is a key intermediate in the synthesis of pharmaceuticals and other bioactive compounds, playing a crucial role in the pharmaceutical industry due to its ability to introduce chirality into molecules and its role in the synthesis of biologically active compounds.

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  • (2S,4R)-4-Hydroxy-1,2-pyrrolidinedicarboxylic acid 2-ethyl-1-(phenylmethyl) ester

    Cas No: 103667-57-8

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  • 103667-57-8 Structure
  • Basic information

    1. Product Name: 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER
    2. Synonyms: 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER;1-Cbz-4-Hydroxy-L-Proline Ethyl Ester;(4R)-1-Benzyl 2-ethyl 4-hydroxypyrrolidine-1,2-dicarboxylate;1-Cbz-trans-4-Hydroxy-L-proline ethyl ester
    3. CAS NO:103667-57-8
    4. Molecular Formula: C15H19NO5
    5. Molecular Weight: 293.31506
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 103667-57-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 434.1±45.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.279±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. PKA: 14.28±0.40(Predicted)
    10. CAS DataBase Reference: 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER(103667-57-8)
    12. EPA Substance Registry System: 1-CBZ-4(R)-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID ETHYL ESTER(103667-57-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 103667-57-8(Hazardous Substances Data)

103667-57-8 Usage

Uses

Used in Pharmaceutical Industry:
1-CBZ-4(R)-Hydroxypyrrolidine-2-carboxylic acid ethyl ester is used as a chiral building block for the synthesis of various pharmaceutical drugs, including antivirals, antifungals, and anti-infective agents. Its chiral nature allows for the creation of enantiomerically pure compounds, which is essential for the development of effective and safe medications.
Used as a Precursor in Peptide-based Drug Production:
In the field of peptide-based drug development, 1-CBZ-4(R)-Hydroxypyrrolidine-2-carboxylic acid ethyl ester serves as a valuable precursor. Its incorporation into peptide structures can enhance the pharmacological properties of the resulting drugs, such as improving their stability, bioavailability, and targeting specific biological receptors.
Used in the Synthesis of Biologically Active Compounds:
1-CBZ-4(R)-Hydroxypyrrolidine-2-carboxylic acid ethyl ester is also utilized in the synthesis of other biologically active compounds, contributing to the development of novel therapeutic agents with potential applications in various medical fields. Its versatility in chemical reactions and ability to introduce chirality make it a sought-after compound in medicinal chemistry research and drug discovery processes.

Check Digit Verification of cas no

The CAS Registry Mumber 103667-57-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,3,6,6 and 7 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 103667-57:
(8*1)+(7*0)+(6*3)+(5*6)+(4*6)+(3*7)+(2*5)+(1*7)=118
118 % 10 = 8
So 103667-57-8 is a valid CAS Registry Number.

103667-57-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-O-benzyl 2-O-ethyl (4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

1.2 Other means of identification

Product number -
Other names 1-Cbz-trans-4-Hydroxy-L-proline ethyl ester

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:103667-57-8 SDS

103667-57-8Relevant articles and documents

Nazumazoles A-C, cyclic pentapeptides dimerized through a disulfide bond from the marine sponge theonella swinhoei

Fukuhara, Kazuya,Takada, Kentaro,Okada, Shigeru,Matsunaga, Shigeki

supporting information, p. 2646 - 2648 (2015/06/16)

A mixture of nazumazoles A-C (1-3) was purified from the extract of the marine sponge Theonella swinhoei. The mixture was eluted as an extraordinarily broad peak in the reversed-phase HPLC. The structures of nazumazoles were determined by interpretation o

SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS

-

Paragraph 01295; 01296, (2015/04/28)

The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE

-

Page/Page column 160, (2013/07/19)

The present invention relates to heterocyclic compounds useful for antagonising angiotensin II Type 2 (AT2) receptor. More particularly the invention relates to pyrrolidine and azetidine compounds, compositions containing them and their use in methods of treating or preventing disorders or diseases associated with AT2 receptor function including neuropathic pain, inflammatory pain, conditions associated with neuronal hypersensitivity, impaired nerve conduction velocity, cell proliferation disorders, disorders associated with an imbalance between bone resorption and bone formation and disorders associated with aberrant nerve regeneration.

Thrombin inhibitors from the freshwater cyanobacterium Anabaena compacta

Anas, Andrea Roxanne J.,Kisugi, Takaya,Umezawa, Taiki,Matsuda, Fuyuhiko,Okino, Tatsufumi,Campitelli, Marc R.,Quinn, Ronald J.

, p. 1546 - 1552,7 (2012/12/12)

Bioassay-guided investigation of the cyanobacterium Anabaena compacta extracts afforded spumigin J (1) and the known thrombin inhibitor spumigin A (2). The absolute configuration of 1 was analyzed by advanced Marfey's methodology. Compounds 1 and 2 inhibi

Thrombin inhibitors from the freshwater cyanobacterium Anabaena compacta

Anas, Andrea Roxanne J.,Kisugi, Takaya,Umezawa, Taiki,Matsuda, Fuyuhiko,Campitelli, Marc R.,Quinn, Ronald J.,Okino, Tatsufumi

, p. 1546 - 1552 (2013/01/15)

Bioassay-guided investigation of the cyanobacterium Anabaena compacta extracts afforded spumigin J (1) and the known thrombin inhibitor spumigin A (2). The absolute configuration of 1 was analyzed by advanced Marfey's methodology. Compounds 1 and 2 inhibi

Synthesis of the four isomers of 4-aminopyrrolidine-2,4-dicarboxylate: Identification of a potent, highly selective, and systemically-active agonist for metabotropic glutamate receptors negatively coupled to adenylate cyclase

Monn, James A.,Valli, Matthew J.,Johnson, Bryan G.,Salhoff, Craig R.,Wright, Rebecca A.,Howe, Trevor,Bond, Ann,Lodge, David,Spangle, Larry A.,Paschal, Jonathan W.,Campbell, Jack B.,Griffey, Kelly,Tizzano, Joseph P.,Schoepp, Darryle D.

, p. 2990 - 3000 (2007/10/03)

The four isomers of 4-aminopyrrolidine-2,4-dicarboxylate (APDC) were prepared and evaluated for their effects at glutamate receptors in vitro. (2R,4R)-APDC (2a), an aza analog of the nonselective mGluR agonist (1S,3R)- 1-aminocyclopentane-1,3-dicarboxylat

Conformationally Defined Neurotransmitter Analogues. Selective Inhibition of Glutamate Uptake by One Pyrrolidine-2,4-dicarboxylate Diastereomer

Bridges, Richard J.,Stanley, Mark S.,Anderson, Michael W.,Cotman, Carl W.,Chamberlin, A. Richard

, p. 717 - 725 (2007/10/02)

In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared.These "conformer mimics", the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of -L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites.While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport.These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.

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