203866-16-4

Basic information

• Product Name: N-Boc-cis-4-Fluoro-L-proline methyl ester
• Synonyms: N-Boc-cis-4-Fluoro-L-proline methyl ester;N-(tert-Butoxycarbonyl)-(2S,4S)-4-fluoroproline Methyl ester;1-tert-butyl 2-Methyl (2S,4S)-4-fluoro-1,2-pyrrolidinedicarboxylate;N-t-BOC-cis-4-fluoro-L-proline methyl ester;1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate;(2S,4S)-4-Fluoro-1,2-pyrrolidinedicarboxylic acid 1-(tert-butyl) 2-methyl ester
• CAS NO: 203866-16-4
• Molecular Formula: C₁₁H₁₈FNO₄
• Molecular Weight: 247.2633232
• Mol File: 203866-16-4.mol

Chemical Properties

• Melting Point: 210 °C
• Boiling Point: 296.525 °C at 760 mmHg
• Flash Point: 110℃
• Appearance: /
• Density: 1.153
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.448
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -5.68±0.60(Predicted)
• CAS DataBase Reference: N-Boc-cis-4-Fluoro-L-proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-cis-4-Fluoro-L-proline methyl ester(203866-16-4)
• EPA Substance Registry System: N-Boc-cis-4-Fluoro-L-proline methyl ester(203866-16-4)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 203866-16-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Boc-cis-4-Fluoro-L-proline methyl ester is used as a key intermediate in the synthesis of various pharmaceutical compounds. The presence of the fluorine atom and the protecting groups allows for selective reactions and the formation of complex molecular structures, contributing to the development of new drugs with improved properties.
Used in Agrochemical Synthesis:
In the agrochemical industry, N-Boc-cis-4-Fluoro-L-proline methyl ester serves as a building block for the creation of novel agrochemicals. Its unique structure and functional groups enable the synthesis of compounds with enhanced biological activity and selectivity, leading to more effective and environmentally friendly products.
Used in Organic Synthesis Research:
N-Boc-cis-4-Fluoro-L-proline methyl ester is utilized as a model compound in organic synthesis research. Its reactivity and structural features provide insights into the development of new synthetic methods and strategies, advancing the field of organic chemistry and enabling the discovery of innovative applications.

InChI:InChI=1/C11H18FNO4/c1-11(2,3)17-10(15)13-6-7(12)5-8(13)9(14)16-4/h7-8H,5-6H2,1-4H3/t7-,8-/m0/s1

Upstream product

• 38078-09-0 diethylamino-sulfur trifluoride 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 220405-40-3 2,2-difluoro-1,3-dimethyl-imidazolidine 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72180-14-4 N-<(phenylmethoxy)carbonyl>-4(S)-fluoro-(S)-proline methyl ester 
• 3674-54-2 tetrabutylammonium thiocyanate 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 88043-21-4 (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 189160-59-6 N-tert-butoxycarbonyl-trans-4-(trifluoromethylsulfonyloxy)-L-proline methyl ester 
• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 1313017-51-4 (2S,4S)-methyl 4-fluoropyrrolidine-2-carboxylate 
• 871979-18-9 3-[2-(1-tert-butoxycarbonyl-(4S)-fluoro-(2S)-pyrrolidinyl)-5-thiazolyl]propionic acid methyl ester 
• 871979-19-0 3-[2-((4S)-fluoro-(2S)-pyrrolidinyl)-5-thiazolyl]propionic acid methyl ester hydrochloride 
• 1613055-45-0 C₄₅H₅₀F₂N₆O₄ 
• 1613055-43-8 C₂₂H₃₁BFN₃O₄ 
• 1613055-40-5 C₁₆H₁₉BrFN₃O₂ 
• 1613055-38-1 C₃₀H₃₁F₄N₃O₅S 
• 1580456-83-2 (2S,4S)-1-[(2S)-2-amino-3-(6-bromobenzo[d][1,3]dioxol-5-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 
• 1580456-81-0 (2S,4S)-1-[(2S)-2-amino-3-(2-(thiophen-2-yl)thiazol-4-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 
• 1580456-78-5 (2S,4S)-1-[(2S)-2-amino-3-(2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 
• 1580456-76-3 (2S,4S)-1-[(2S)-2-amino-3-(2-(4-chlorophenyl)thiazol-4-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 
• 1580456-74-1 (2S,4S)-1-[(2S)-2-amino-3-(2-phenylthiazol-4-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 
• 1580456-72-9 (2S,4S)-1-[(2S)-2-amino-3-(2-methylthiazol-4-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 
• 1580456-70-7 (2S,4S)-1-[(2S)-2-amino-3-(thiazol-4-yl)propanoyl]-4-fluoropyrrolidine-2-carbonitrile 

Relevant articles and documents

Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB)

Herein we report the first X-ray crystal structure of the well-known (S)-l-ala-Ni-BPB complex (1) and compare this with the X-ray crystal structures obtained for two novel fluorinated (S)-l-ala-Ni-BPB complexes (8 and 12) that contain either an S- or R-fluorine atom on the proline ring of the BPB ligand. The preparation of complexes 8 and 12 has been enabled by the synthesis of two new fluorinated BPB ligands (7 and 11). In this work we looked to observe the structural effects that the introduction of a single fluorine atom had on the known complex 1. Arising from this, we highlight a novel fluorine-nickel interaction that on the basis of DFT calculations appears to provide additional stabilization to one of the complexes prepared ((S)-l-ala-Ni-BPB complex 8).

COMPOUNDS TARGETING RNA-BINDING PROTEINS OR RNA-MODIFYING PROTEINS

The invention relates to a compound represented by Formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising the same and methods of preparing and using the same. The variables are described herein.

Large-Scale Practical Synthesis of Boc-Protected 4-Fluoro-l-Proline

A large-scale synthesis process of N-Boc-4-fluoro-l-proline (1) from N-Boc-4-hydroxy-l-proline methyl ester (2) using nosyl fluoride (13) as a deoxyfluorinating agent has been developed. An eco-friendly and large-scale feasible process using a single solvent was developed to afford moderate yields of products with excellent purity >99% by high-performance liquid chromatography. The key feature of the optimization involving chromatography-free purification and isolation on a kilogram-scale at a pilot plant scale is described.

Novel Tricyclic Pyroglutamide Derivatives as Potent RORγt Inverse Agonists Identified using a Virtual Screening Approach

Employing a virtual screening approach, we identified the pyroglutamide moiety as a nonacid replacement for the cyclohexanecarboxylic acid group which, when coupled to our previously reported conformationally locked tricyclic core, provided potent and selective RORγt inverse agonists. Structure-activity relationship optimization of the pyroglutamide moiety led to the identification of compound 18 as a potent and selective RORγt inverse agonist, albeit with poor aqueous solubility. We took advantage of the tertiary carbinol group in 18 to synthesize a phosphate prodrug, which provided good solubility, excellent exposures in mouse PK studies, and significant efficacy in a mouse model of psoriasis.

Rapid Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature

The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf-stable, easy-to-handle, fluorine-economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi-dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2-pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine-economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.

BENZIMIDAZOLE-LINKED INDOLE COMPOUND ACTING AS NOVEL DIVALENT IAP ANTAGONIST

The present invention discloses a benzimidazole-linked indole compound acting as novel divalent IAP antagonist, specifically disclosing the compound shown in fomulas (I) or a pharmaceutically acceptable salt thereof.

Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor

Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.

HETEROCYCLIC DERIVATIVES AS ANTIBACTERIAL COMPOUNDS

Compounds of Formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof, their preparation, pharmaceutical compositions comprising such compounds and their use in treating and/or preventing bacterial infections are disclosed.

Synthesis and antibacterial activity of 6(R)- and 6(S)-fluoropenibruguieramine As: Fluorine as a probe for testing the powerfulness of memory of chirality (MOC)

The synthesis of 6(R)- and 6(S)- fluoropenibruguieramine As has been achieved, employing the elegant strategy developed by Kim and co-workers. Single diastereomers were formed via the key intramolecular aldol reaction, and both of the products were unambiguously confirmed by X-ray diffraction crystallography. This reaction shows that the fluorine amide effect could not compete with the memory of chirality (MOC) effect, thus further demonstrating the powerfulness of MOC effect in asymmetric synthesis. The biological testing carried out in this work indicates that the principal of antibacterial activity of the natural extract is probably not penibruguieramine A.

Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: Towards antifreeze molecules

Galactose-conjugated fluorinated and non-fluorinated proline oligomers that exhibit an α-helical structure with hydrophilic and lipophilic parts were designed as potential antifreeze molecules. These galactose-proline oligomers were synthesized and their physical properties were evaluated. Interestingly, the non-fluorinated galactose-proline oligomers showed in contrast to the fluorinated analogues weak antifreeze activity. The difference in antifreeze activity should be attributed to the fluorine gauche effect, which should induce a conformation in fluorinated prolines that is different from that of natural proline. The results obtained in this study thus suggest that the 3D conformation of the galactose-conjugated fluorinated and non-fluorinated proline oligomers is very important for their anti-freezing properties.