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Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate is a chemical compound that is a derivative of the amino acid proline. It is commonly used in organic synthesis and medicinal chemistry as a chiral building block in the synthesis of pharmaceuticals and biologically active molecules. The Boc (tert-butoxycarbonyl) protecting group helps to prevent unwanted reactions at specific sites on the molecule, while the benzyl group provides stability and solubility. This versatile intermediate can be utilized in the preparation of a wide range of pharmaceutical and agrochemical products.

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  • 154456-97-0 Structure
  • Basic information

    1. Product Name: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate
    2. Synonyms: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate;2-benzyl 1-(tert-butyl) 4-oxopyrrolidine-1,2-dicarboxylate;(S)-4-Oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester;N-(tert-butyloxycarbonyl)-4-oxoproline benzyl ester;(S)-2-benzyl1-tert-butyl4-oxopyrrolidine-1,2-dicarboxylate(WXC07842)
    3. CAS NO:154456-97-0
    4. Molecular Formula: C17H21NO5
    5. Molecular Weight: 319.36
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 154456-97-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 439.9±45.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.219±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: -3.90±0.40(Predicted)
    10. CAS DataBase Reference: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate(CAS DataBase Reference)
    11. NIST Chemistry Reference: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate(154456-97-0)
    12. EPA Substance Registry System: Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate(154456-97-0)
  • 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: 154456-97-0(Hazardous Substances Data)

154456-97-0 Usage

Uses

Used in Pharmaceutical Industry:
Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate is used as a chiral building block for the synthesis of pharmaceuticals and biologically active molecules. Its unique structure and protecting group make it a valuable component in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Benzyl (S)-1-Boc-4-oxo-2-pyrrolidinecarboxylate is also used as an intermediate in the synthesis of agrochemical products. Its versatility allows it to be incorporated into the development of various agrochemicals, contributing to advancements in agriculture and pest control.

Check Digit Verification of cas no

The CAS Registry Mumber 154456-97-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,4,4,5 and 6 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 154456-97:
(8*1)+(7*5)+(6*4)+(5*4)+(4*5)+(3*6)+(2*9)+(1*7)=150
150 % 10 = 0
So 154456-97-0 is a valid CAS Registry Number.

154456-97-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(tert-butyloxycarbonyl)-4-oxoproline benzyl ester

1.2 Other means of identification

Product number -
Other names benzyl (2S,4R)-N-tert-butoxycarbonyl-4-oxoprolinate

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:154456-97-0 SDS

154456-97-0Relevant articles and documents

A Novel Entry to Carbenoid Species via β-Ketosulfoxonium Ylides

Baldwin, Jack E.,Adlington, Robert M.,Godfrey, Christopher R. A.,Gollins, David W.,Vaughan, Jason G.

, p. 1434 - 1435 (1993)

In the presence of suitable rhodium(II) catalysts, lactam derived β-ketosulfoxonium ylides can be transformed to β-oxonitrogen heterocycles, e. g. substituted 4-oxopyrrolidine, via intermediates of carbenoid nature.

Tetrahydropyridopyrimidine compound with anti-tumor activity

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Paragraph 0604-0608, (2020/12/30)

The invention provides a tetrahydropyridopyrimidine compound shown as a formula (I) or a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the tetrahydropyridopyrimidine compound and the pharmaceutically acceptable salt thereof, and application of the tetrahydropyridopyrimidine compound or the pharmaceutically acceptable salt thereof in the preparation of a drug forpreventing and/or treating KRAS G12C mutant tumors.

Synthesis and Conformational Properties of 3,4-Difluoro- l -prolines

Hofman, Gert-Jan,Ottoy, Emile,Light, Mark E.,Kieffer, Bruno,Martins, Jose C.,Kuprov, Ilya,Sinnaeve, Davy,Linclau, Bruno

, p. 3100 - 3120 (2019/03/11)

Fluorinated proline derivatives have found diverse applications in areas ranging from medicinal chemistry over structural biochemistry to organocatalysis. Depending on the stereochemistry of monofluorination at the proline 3- or 4-position, different effe

FLUOROHYDROXYPROLINE DERIVATIVES USEFUL IN THE PREPARATION OF PROTEOLYSIS TARGETED CHIMERAS

-

Page/Page column 46; 72, (2018/04/14)

There is provided novel small molecule E3 ubiquitin ligase protein binding ligand compounds, and to their utility in PROteolysis Targeted Chimeras (PROTACs), as well as processes for their preparation thereof, and use in medicine. There is particularly provided novel small molecule E3 ubiquitin ligase protein binding inhibitorcompounds based on a fluorohydroxyproline scaffold, to their utility as ligands in synthesizing novel PROTACs, and to synthetic methods therefor.

Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode

Jurica, Elizabeth A.,Wu, Ximao,Williams, Kristin N.,Hernandez, Andres S.,Nirschl, David S.,Rampulla, Richard A.,Mathur, Arvind,Zhou, Min,Cao, Gary,Xie, Chunshan,Jacob, Biji,Cai, Hong,Wang, Tao,Murphy, Brian J.,Liu, Heng,Xu, Carrie,Kunselman, Lori K.,Hicks, Michael B.,Sun, Qin,Schnur, Dora M.,Sitkoff, Doree F.,Dierks, Elizabeth A.,Apedo, Atsu,Moore, Douglas B.,Foster, Kimberly A.,Cvijic, Mary Ellen,Panemangalore, Reshma,Flynn, Neil A.,Maxwell, Brad D.,Hong, Yang,Tian, Yuan,Wilkes, Jason J.,Zinker, Bradley A.,Whaley, Jean M.,Barrish, Joel C.,Robl, Jeffrey A.,Ewing, William R.,Ellsworth, Bruce A.

, p. 1417 - 1431 (2017/03/08)

A novel series of pyrrolidine-containing GPR40 agonists is described as a potential treatment for type 2 diabetes. The initial pyrrolidine hit was modified by moving the position of the carboxylic acid, a key pharmacophore for GPR40. Addition of a 4-cis-CF3 to the pyrrolidine improves the human GPR40 binding Ki and agonist efficacy. After further optimization, the discovery of a minor enantiomeric impurity with agonist activity led to the finding that enantiomers (R,R)-68 and (S,S)-68 have differential effects on the radioligand used for the binding assay, with (R,R)-68 potentiating the radioligand and (S,S)-68 displacing the radioligand. Compound (R,R)-68 activates both Gq-coupled intracellular Ca2+ flux and Gs-coupled cAMP accumulation. This signaling bias results in a dual mechanism of action for compound (R,R)-68, demonstrating glucose-dependent insulin and GLP-1 secretion in vitro. In vivo, compound (R,R)-68 significantly lowers plasma glucose levels in mice during an oral glucose challenge, encouraging further development of the series.

ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

-

Paragraph 0572, (2017/03/14)

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an aryl, heteroaryl or heterocycle (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

-

, (2008/06/13)

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines

Qiu, Xiao-long,Qing, Feng-ling

, p. 7162 - 7164 (2007/10/03)

A short, efficient, and diastereomerically pure synthesis of N-Boc-cis-4-trifluoromethyl-L-proline (7) and N-Boc-cis-4-difluoromethyl-L-proline (9) from N-Boc-4-oxo- L-proline (4) is described. The reaction of 4 with Me3SiCF3 and the conversion of the carbonyl group of 4 into the difluoromethylene group are the key steps for the synthesis of 7 and 9, respectively.

Stereoselective synthesis of novel chimerical amino acids via a photochemical key step

Wessig, Pablo

, p. 1465 - 1467 (2007/10/03)

The synthesis of novel chimerical amino acid derivatives 6-8 bearing the 6-azatricyclo[3.3.1.033,7]nonane (methanotropane) skeleton is described. Starting with one chirality centre in L-4-oxoprolines 2 we succeeded in the fully stereoselective introduction of four new chirality centres. The key step of our synthetic route is a photochemical cyclization of phenyl ketones, whose stereoselectivity has been explained by the different stability of the triplet biradical conformers.

Synthesis of kainoid analogues

Barraclough, Paul,Hudhomme, Pietrick,Spray, Caroline A.,Young, Douglas W.

, p. 4195 - 4212 (2007/10/02)

4-oxoproline has been used as a chiral template in a synthesis of kainoid analogues which are epimeric with the parent compound at C-3.

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