220993-22-6

Basic information

• Product Name: (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester
• Synonyms: (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester
• CAS NO: 220993-22-6
• Molecular Formula: C₁₆H₃₁NO₄Si
• Molecular Weight: 329.50714
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 220993-22-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester(220993-22-6)
• EPA Substance Registry System: (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester(220993-22-6)

Safety Data

• Hazardous Substances Data: 220993-22-6(Hazardous Substances Data)

Usage

Description

(2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester is a complex organic compound with a unique molecular structure. It is characterized by a chiral center at the 2-position, a tert-butyl ester group, and a silyl ether protecting group. (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester serves as an intermediate in the synthesis of various pharmaceuticals and bioactive molecules.

Uses

Used in Pharmaceutical Industry:
(2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester is used as a key intermediate in the synthesis of oxazolidinone derivatives, which are a class of antibiotics with potent antibacterial activity. These derivatives are effective against a wide range of gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester's unique structure allows for the development of new antibiotics with improved properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Antibacterial Applications:
(2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester is used as a precursor for the preparation of antibacterial oxazolidinone derivatives. These derivatives exhibit broad-spectrum antibacterial activity and are particularly useful in treating infections caused by drug-resistant bacteria. (2S)-2-[[tert-ButyldiMethylsilyloxy]Methyl]-4-oxo-1-pyrrolidinecarboxylic Acid tert-Butyl Ester's role in the synthesis of these derivatives is crucial for the development of new and effective antibacterial agents to combat the growing threat of antibiotic resistance.

Upstream product

• 61478-26-0 tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 51-35-4 4R-4-hydroxyproline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 125653-58-9 (2S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 540501-65-3 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(phenylthio)methylenepyrrolidine 
• 540501-44-8 (2S,4R)-N-tert-butyloxycarbonyl-4-(4'-ethoxy)benzyl-2-hydroxymethylpyrrolidine 
• 540501-39-1 (S)-4-[1-(4-Ethoxy-phenyl)-meth-(E)-ylidene]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 83623-78-3 (2S,4S)-4-benzyl-N-tert-butyloxycarbonylproline 
• 153074-95-4 (2S,4R)-4-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 540501-64-2 (2S,4R)-N-tert-butyloxycarbonyl-4-(methoxycarbonyl)methylproline 
• 540501-64-2 (2S,4S)-N-tert-butyloxycarbonyl-4-(methoxycarbonyl)methylproline 
• 540501-37-9 (S)-2-Hydroxymethyl-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 540501-43-7 (2S,4R)-N-tert-butyloxycarbonyl-4-benzyl-2-hydroxymethylpyrrolidine 
• 540501-62-0 (2S,4S)-N-tert-butyloxycarbonyl-4-propylproline 
• 540501-47-1 (2S,4R)-N-tert-butyloxycarbonyl-4-propylproline 
• 540501-56-2 (2S,4S)-tert-butyl 2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate 
• 364750-80-1 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid 
• 540501-28-8 (S)-2-tert-butyldimethylsilyloxymethyl-N-tert-butyloxycarbonyl-4-(4'-ethoxyphenyl)methylenepyrrolidine 

Relevant articles and documents

Design, Synthesis, and Pharmacological Evaluation of Potent Positive Allosteric Modulators of the Glucagon-like Peptide-1 Receptor (GLP-1R)

The therapeutic success of peptidic GLP-1 receptor agonists for treatment of type 2 diabetes mellitus (T2DM) motivated our search for orally bioavailable small molecules that can activate the GLP-1 receptor (GLP-1R) as a well-validated target for T2DM. Here, the discovery and characterization of a potent and selective positive allosteric modulator (PAM) for GLP-1R based on a 3,4,5,6-tetrahydro-1H-1,5-epiminoazocino[4,5-b]indole scaffold is reported. Optimization of this series from HTS was supported by a GLP-1R ligand binding model. Biological in vitro testing revealed favorable ADME and pharmacological profiles for the best compound 19. Characterization by in vivo pharmacokinetic and pharmacological studies demonstrated that 19 activates GLP-1R as positive allosteric modulator (PAM) in the presence of the much less active endogenous degradation product GLP1(9-36)NH2 of the potent endogenous ligand GLP-1(7-36)NH2. While these data suggest the potential of small molecule GLP-1R PAMs for T2DM treatment, further optimization is still required towards a clinical candidate.

Antibiotic oxazolidinone derivatives

The invention concerns a compound of the formula (I): wherein, for example:T is of the formula (IA), (IB), or (IC); R1 is of the formula —NHC(=O)Rb wherein Rb is (1-4C)alkyl;R2 and R3 are hydrogen or