92235-34-2

Basic information

• Product Name: (S)-BOC-3-AMINO-2-PYRROLIDINONE
• Synonyms: (S)-BOC-3-AMINO-2-PYRROLIDINONE;(S)-(-)-3-BOC-AMINOPYRROLIDIN-2-ONE;CarbaMic acid, N-[(3S)-2-oxo-3-pyrrolidinyl]-, 1,1-diMethylethyl ester;tert-butyl 2-oxopyrrolidin-3-ylcarbaMate;(S)-tert-butyl 2-oxopyrrolidin-3-ylcarbaMate;(2-oxopyrrolidin-3-(S)-yl)carbaMic acid tert-butyl ester;2-Methyl-2-propanyl [(3S)-2-oxo-3-pyrrolidinyl]carbaMate;tert-butyl (S)-(2-oxopyrrolidin-3-yl)carbamate
• CAS NO: 92235-34-2
• Molecular Formula: C₉H₁₆N₂O₃
• Molecular Weight: 200.23
• Product Categories: pharmacetical;Amino Acids & Deriv.;CHIRAL CHEMICALS
• Mol File: 92235-34-2.mol

Chemical Properties

• Melting Point: 168.0-170.3 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• Boiling Point: 394.033oC at 760 mmHg
• Flash Point: 192.105oC
• Appearance: /
• Density: 1.138g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: 2-8°C
• PKA: 11.05±0.20(Predicted)
• CAS DataBase Reference: (S)-BOC-3-AMINO-2-PYRROLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-BOC-3-AMINO-2-PYRROLIDINONE(92235-34-2)
• EPA Substance Registry System: (S)-BOC-3-AMINO-2-PYRROLIDINONE(92235-34-2)

Safety Data

• Hazardous Substances Data: 92235-34-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-BOC-3-AMINO-2-PYRROLIDINONE is used as a building block for the synthesis of various pharmaceutical compounds and drug candidates. Its BOC protecting group allows for selective reactions and the creation of complex molecular structures, contributing to the development of novel therapeutic agents.
Used in Biotechnology Industry:
In the biotechnology field, (S)-BOC-3-AMINO-2-PYRROLIDINONE is utilized as a chiral auxiliary in asymmetric synthesis. This application aids in the production of enantiomerically pure compounds, which are essential for the biological activity and selectivity of many pharmaceuticals.
Used as a Precursor in Peptidomimetics Preparation:
(S)-BOC-3-AMINO-2-PYRROLIDINONE also serves as a precursor in the preparation of peptidomimetics, which are compounds that mimic the structure and function of peptides. These peptidomimetics have potential applications in drug discovery, offering advantages such as increased stability and bioavailability compared to traditional peptides.

InChI:InChI=1/C9H16N2O3/c1-9(2,3)14-8(13)11-6-4-5-10-7(6)12/h6H,4-5H2,1-3H3,(H,10,12)(H,11,13)/t6-/m0/s1

Upstream product

• 13726-85-7 Boc-Gln-OH 
• 25691-37-6 (2S)-4-amino-2-[(tert-butoxycarbonyl)amino]butanoic acid 

Downstream Products

• 205055-67-0 3-(S)-(tert-butoxycarbonylamino)-1-(5-bromo-2-fluorobenzyl)pyrrolidin-2-one 
• 245761-08-4 [2-(3-tert-butoxycarbonylamino-2-oxopyrrolidin-1-ylmethyl)-4-cyanophenoxy]acetic acid methyl ester 
• 205055-05-6 3-(S)-(tert-butoxycarbonylamino)-1-(5-iodo-2-(2-methoxyethoxymethoxy)benzyl)pyrrolidin-2-one 
• 186552-00-1 {1-[3-(benzhydrylidenylamino)-5-cyanobenzyl]-2-oxopyrrolidin-3-yl}carbamic acid tert-butylester 
• 186551-91-7 {1-[2-(benzhydrylidenylamino)-5-cyanobenzyl]-2-oxopyrrolidin-3-yl}carbamic acid tert-butyl ester 
• 251936-86-4 [1(-3-Amino-4-cyanobenzyl)-2-oxopyrrolidin-3-(S)-yl]carbamic acid tert-butyl ester 
• 1400580-82-6 tert-butyl ((S)-1-(3-carbamoyl-4-(((R)-1-(4-cyanophenyl)-3,3-dimethylpiperidin-4-yl)amino)pyrrolo[1,2-b]pyridazin-6-yl)-2-oxopyrrolidin-3-yl)carbamate 
• 859213-21-1 ethyl 4-[(S)-3-(t-butoxycarbonylamino)-2-oxopyrrolidin-1-ylmethyl]-3-trifluoromethylbenzoate 
• 209286-33-9 [1-(4-nitrobenzyl)-2-oxopyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester 
• 209286-82-8 [1-(1-benzenesulfonyl-4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxopyrrolid-3-(S)-yl]-carbamic acid tert-butyl ester 
• 251936-50-2 [1-(2-amino-ethyl)-2-oxo-pyrrolidin-3-yl]-carbamic acid tert-butyl ester 
• 92235-35-3 (S)-tert-butyl 1-methyl-2-oxopyrrolidin-3-ylcarbamate 
• 245761-02-8 3-(S)-(tert-butoxycarbonylamino)-1-(3-iodo-4-(2-methoxyethoxymethoxy)benzyl)pyrrolidin-2-one 
• 209286-14-6 {1-[6-(benzhydrylidene-amino)-1-chloro-isoquinolin-7-ylmethyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid tert-butyl ester 

Relevant articles and documents

Protein synthesis with conformationally constrained cyclic dipeptides

We have synthesized several conformationally constrained dipeptide analogues as possible substrates for incorporation into proteins. These have included three cyclic dipeptides formed from Boc derivatives of 2,4-diaminobutyric acid, ornithine and lysine, having 5-, 6-, and 7-membered lactam rings, respectively. These dipeptides were used to activate a suppressor tRNA transcript, the latter of which had been prepared by in vitro transcription. Using modified E. coli ribosomes described previously, these activated suppressor tRNAs enabled the incorporation of the three cyclic dipeptides into dihydrofolate reductase (DHFR) at positions 18 and 49. The suppression yields increased with increasing lactam ring size and were found to proceed in suppression yields ranging from 3.4 to 8.9% at two different protein sites for the 5-, 6- and 7-membered lactam dipeptides. The greater facility of incorporation of the 7-membered lactam prompted us to prepare two 7-membered cyclic acylhydrazides (4 and 5) by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI)-mediated cyclization of amino acids having selectively protected hydrazine functional groups in their side chains. In common with the lactam dipeptides, acylhydrazide dipeptides 4 and 5 could be used to activate the same suppressor tRNA transcript and to incorporate the cyclic dipeptides into DHFR. They were incorporated into the same two DHFR sites in suppression yields ranging from 8.3 to 11.2%.

RIBOSOME-MEDIATED INCORPORATION OF PEPTIDES AND PEPTIDOMIMETICS

Modified ribosomes that were selected using a dipeptidyl-puromycin aminonucleoside are used to mediate site-specific incorporation of one or more peptides and peptidomimetics into protein in a cell free translation system. In addition, new fluorescent dipeptidomimetics have been synthesized and incorporated into proteins, as well as modified proteins containing one or more non-naturally occurring dipeptides.

Concise and efficient synthesis of highly potent and selective dipeptidyl peptidase II inhibitors

Highly potent and selective DPP II inhibitors N'-(4-Chlorobenzyl)-N'- methyl-4-oxo-4-(1-piperidinyl)-1,3-(S)-butane-diamine dihydrochloride 1 and N'-(4-chlorobenzyl)-4-oxo-4-(1-piperidinyl)-1,3-(S)-butanediamine dihydrochloride 2 have been efficiently synthesized starting from L-glutamine. A short and high yielding route with simple isolation techniques has been disclosed. Copyright Taylor & Francis Group, LLC.

Synthesis, SAR and in vivo activity of novel thienopyridine sulfonamide pyrrolidinones as factor Xa inhibitors

Thienopyridine sulfonamide pyrrolidinones were found to be potent and selective inhibitors of the coagulation cascade enzyme factor Xa. SAR studies led to several compounds that were selected for further in vivo investigation. These novel aryl binding pocket moieties represent a structural modification to a series of fXa inhibitors. Several compounds proved to be efficacious iv antithrombotic agents.

Design and structure-activity relationships of potent and selective inhibitors of blood coagulation factor Xa

The discovery of a series of non-peptide factor Xa (FXa) inhibitors incorporating 3-(s)-amino-2-pyrrolidinone as a central template is described. After identifying compound 4, improvements in in vitro potency involved modifications of the liphophilic group and optimizing the angle of presentation of the amidine group to the S1 pocket of FXa. These studies ultimately led to compound RPR120844, a potent inhibitor of FXa (K1 = 7 nM) which shows selectivity for FXa over trypsin, thrombin, and several fibrinolytic serine proteinases. RPR120844 is an effective anticoagulant in both the rat model of FeCl2-induced carotid artery thrombosis and the rabbit model of jugular vein thrombus formation.