74411-97-5

Basic information

• Product Name: (S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID
• Synonyms: (S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID;(S)-2-(3-Boc-amino)-2-oxopiperidin-1-yl)acetic acid;(S)-2-(3-(tert-Butoxycarbonylamino)-2-oxopiperidin-1-yl)acetic aci;{3-[(tert-Butoxycarbonyl)amino]-2-oxopiperidin-1-yl}acetic acid
• CAS NO: 74411-97-5
• Molecular Formula: C₁₂H₂₀N₂O₅
• Molecular Weight: 272.3
• Product Categories: CHIRAL CHEMICALS
• Mol File: 74411-97-5.mol

Chemical Properties

• Melting Point: 110-113 °C
• Boiling Point: 497.878 °C at 760 mmHg
• Flash Point: 254.908 °C
• Appearance: /
• Density: 1.248 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: 2-8°C
• PKA: 3.73±0.10(Predicted)
• CAS DataBase Reference: (S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID(74411-97-5)
• EPA Substance Registry System: (S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID(74411-97-5)

Safety Data

• Hazardous Substances Data: 74411-97-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
(S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID is used as a building block in the synthesis of complex molecules and peptides for pharmaceutical research and drug development. Its versatile reactivity and the presence of functional groups make it a valuable reagent in the creation of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID is used as a key intermediate for the preparation of various organic compounds. Its unique structure and functional groups enable chemists to perform a wide range of chemical transformations, leading to the development of new and innovative organic molecules.
Used in Peptide Chemistry:
(S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID is utilized as a building block in peptide chemistry for the synthesis of peptides and peptide-based drugs. Its incorporation into peptide sequences allows for the exploration of new peptide therapeutics and the enhancement of existing peptide drugs.
Used in Chemical Transformations:
In chemical transformations, (S)-2-(3-(TERT-BUTOXYCARBONYLAMINO)-2-OXOPIPERIDIN-1-YL)ACETICACID is employed as a versatile reagent to facilitate various chemical reactions. Its functional groups enable the compound to participate in a range of transformations, such as esterification, amidation, and other condensation reactions, contributing to the synthesis of diverse organic molecules.

InChI:InChI=1/C12H20N2O5/c1-12(2,3)19-11(18)13-8-5-4-6-14(10(8)17)7-9(15)16/h8H,4-7H2,1-3H3,(H,13,18)(H,15,16)/t8-/m0/s1

Upstream product

• 92235-39-7 3(S)-<(butoxycarbonyl)amino>-2-oxopiperidine 
• 21887-64-9 N₂-(tert-butoxycarbonyl)-L-ornithine 
• 2480-93-5 Boc-Orn(Z)-OH 
• 298-12-4 Glyoxilic acid 
• 175133-83-2 (3S)-benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-yl)acetate 
• 74411-96-4 N^α-(tert-butoxycarbonyl)-N^δ-(carboxymethyl)ornithine 

Downstream Products

• 186261-87-0 C₂₂H₃₃N₇O₇S 
• 201355-23-9 N-((S)-1-Carbamimidoyl-2-ethoxy-piperidin-3-yl)-2-((S)-2-oxo-3-phenylmethanesulfonylamino-piperidin-1-yl)-acetamide 
• 174960-80-6 ((S)-2-Oxo-3-phenylmethanesulfonylamino-piperidin-1-yl)-acetic acid methyl ester 
• 186261-86-9 C₂₁H₃₈N₈O₇S 
• 186261-84-7 C₂₁H₃₁N₇O₇S 
• 186261-80-3 C₁₄H₂₅N₃O₅S 
• 186261-79-0 ((S)-3-Benzenesulfonylamino-2-oxo-piperidin-1-yl)-acetic acid methyl ester 
• 1027161-96-1 ((S)-3-Benzenesulfonylamino-2-oxo-piperidin-1-yl)-acetic acid 
• 1026870-06-3 C₁₃H₂₃N₃O₅S 

Relevant articles and documents

Design, synthesis, and structure-activity relationships of unsubstituted piperazinone-based transition state factor Xa inhibitors

A series of novel transition state factor Xa inhibitors containing a variety of lactam ring systems as central templates was synthesized in an expedient manner and allowed for a great deal of structural variability. Among them, the piperazinone-based inhibitors were found to be not only active against factor Xa but also selective over thrombin. Optimization of the P4 moiety yielded several potent compounds with IC50 below 1 nM against factor Xa.

3-AMINO-2-OXO-1-PIPERIDINEACETIC DERIVATIVES CONTAINING AN ARGININE MIMIC AS ENZYME INHIBITORS

The present invention discloses peptide aldehydes having a lactam group as part of the peptide backbone and having an original mimic group such as an amidinopiperidine or amidinophengyl tail. These compounds are potent and specific inhibitors of thrombin,

Inhibition of human neutrophil elastase. 4. Design, synthesis, X-ray crystallographic analysis, and structure-activity relationships for a series of P2-modified, orally active peptidyl pentafluoroethyl ketones

A series of P2-modified, orally active peptidic inhibitors of human neutrophil elastase (HNE) are reported. These pentafluoroethyl ketone-based inhibitors were designed using pentafluoroethyl ketone 1 as a model. Rational structural modifications were made at the P3, P2, and activating group (A(G)) portions of 1 based on structure-activity relationships (SAR) developed from in vitro (measured K(i)) data and information provided by modeling studies that docked inhibitor 1 into the active site of HNE. The modeling-based design was corroborated with X-ray crystallographic analysis of the complex between 1 and porcine pancreatic elastase (PPE) and subsequently the complex between 1 and HNE.

3-amino-2-oxo-1-piperidineacetic derivatives as enzyme inhibitors

The present invention discloses peptide aldehydes which are potent and specific inhibitors of thrombin, their pharmaceutically acceptable salts, pharmaceutically acceptable compositions thereof, and methods of using them as therapeutic agents for disease

Rational design and synthesis of a novel, selective class of thrombin inhibitors: P1-argininal derivatives incorporating P3-P4 quaternary lactam dipeptide surrogates

SAR and molecular modeling investigations on the potent and selective thrombin inhibitor 1b (CVS 1578) and related serine protease inhibitors led to the design of series 2a-g, featuring quaternary α-amino-α-benzyl-lactam scaffolds that serve as novel P3-P4 dipeptide mimics. The design, synthesis, and biological activity of these targets an presented.

Protected Lactam-Bridged Dipeptides for Use as Conformational Constraints in Peptides

General methods have been devised for the synthesis of lactam-constrained dipeptide analogues having five-, six-, and seven-membered rings.Three different paths from protected chiral α-amino acids to lactams involving intramolecular alkylation, intramolecular acylation, and insertion of a one carbon unit by condensation with formaldehyde have been utilized.The first two methods produce chiral products stereospecifically, but considerable racemization occurs in the third route which leads to a 4-oxo-5-amino-1,3-thiazine (13).The products are prepared in good yield and have protecting groups making them suitable for incorporation into higher peptides by methods commonly used.