203866-13-1

Basic information

• Product Name: N-BOC-cis-4-fluoro-L-proline
• Synonyms: N-TERT-BUTOXYCARBONYL-CIS-4-FLUORO-L-PROLINE;N-T-BOC-CIS-4-FLUORO-L-PROLINE;BOC-CIS-4-FLUORO-L-PROLINE;BOC-CIS-4-FLUORO-PRO-OH;(2S,4S)-BOC-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID;(2S,4S)-4-FLUORO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;(2S,4S)-4-FLUORO-1-TERT-BUTOXYCARBONYL-PYRROLIDINE-2-CARBOXYLIC ACID;(2S,4S)-4-Fluoro-N-Boc-Pyrrolidine-2-carboxylic acid
• CAS NO: 203866-13-1
• Molecular Formula: C₁₀H₁₆FNO₄
• Molecular Weight: 233.24
• Product Categories: Nitrogen cyclic compounds;Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Chiral Building Blocks;Heterocyclic Building Blocks;Pyrrolidines
• Mol File: 203866-13-1.mol

Chemical Properties

• Melting Point: 157-161.°C
• Boiling Point: 346 °C at 760 mmHg
• Flash Point: 163 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 1.05E-05mmHg at 25°C
• Refractive Index: -57 ° (C=1, MeOH)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.53±0.40(Predicted)
• CAS DataBase Reference: N-BOC-cis-4-fluoro-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-cis-4-fluoro-L-proline(203866-13-1)
• EPA Substance Registry System: N-BOC-cis-4-fluoro-L-proline(203866-13-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 203866-13-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-cis-4-fluoro-L-proline is used as a key building block for the synthesis of various bioactive peptides and peptidomimetics. Its incorporation into peptide sequences allows for the development of novel therapeutic agents with improved pharmacological properties.
Used in Medicinal Chemistry Research:
As a substrate, N-BOC-cis-4-fluoro-L-proline is utilized in the preparation of α4β2 Receptor ligands that possess a pyrrolidine nucleus. These ligands are important for studying and modulating neuronal nicotinic acetylcholine receptors, which play a crucial role in various physiological processes and are implicated in several neurological disorders.
Used in Drug Discovery:
N-BOC-cis-4-fluoro-L-proline is also used in the synthesis of β-amino pyrrolidine-2-carbonitrile derivatives. These compounds have potential as dipeptidyl peptidase IV (DPP4) inhibitors, which are of interest in the treatment of type 2 diabetes and other metabolic disorders. By inhibiting DPP4, these derivatives can help regulate glucose levels and improve insulin sensitivity.

InChI:InChI=1/C10H16FNO4/c1-10(2,3)16-9(15)12-5-6(11)4-7(12)8(13)14/h6-7H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m0/s1

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 72180-14-4 N-<(phenylmethoxy)carbonyl>-4(S)-fluoro-(S)-proline methyl ester 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 74844-93-2 N-BOC-3,4-didehydro-(S)-proline methyl ester 
• 83548-46-3 (S)-1-tert-butyl 2-methyl 2,3-dihydro-1H-pyrrole-1,2-dicarboxylate 
• 203866-16-4 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 587888-04-8 N-tert-butoxycarbonyl-(2S,4S)-4-fluoroproline benzyl ester 

Downstream Products

• 2438-57-5 (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid 
• 1445591-84-3 C₁₈H₂₁BrFN₃O₂ 
• 1560643-01-7 C₂₄H₃₃BFN₃O₄ 
• 1560643-02-8 C₃₀H₃₁F₄N₃O₅S 
• 1560643-05-1 C₃₅H₄₃BFN₃O₄ 
• 1560643-08-4 C₄₁H₄₈F₂N₆O₄ 
• 1560649-18-4 C₄₅H₅₄F₂N₈O₆ 
• 1560642-96-7 C₁₇H₂₁BrFNO₄ 
• 596817-06-0 (2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile 
• 1001354-51-3 (2S,4S)-4-fluoropyrrolidine-2-carboxylic acid hydrochloride 
• 479253-00-4 tert-butyl (S)-3-fluoropyrrolidine-1-carboxylate 

Relevant articles and documents

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.

West request acid bei geleg sandbank and intermediate preparation method

The invention relates to a preparation method of besigliptin and its intermediate, and concretely relates to a preparation method of an azadicyclic compound besigliptin and its key intermediate. The preparation method comprises the following steps: carrying out step a, step b and step c to prepare the key intermediate compound of formula VII, carryin gout isomer resolution and protective group removal on the compound of formula VII to obtain a compound of formula XV, coupling the compound of formula XV with the compound of formula XIII, and salifying to form a target compound I. The preparation method has the advantages of substantial reduction of the production cost, simple production flow, yield increase, and suitableness for industrial production.

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.

As hepatitis c inhibitor spiro compound and its use in medicine

The invention provides a spiro compound serving as a hepatitis c inhibitor and application thereof in a medicine. The compound is a compound as shown in a formula (I) or a stereisomer, a geometric isomer, a tautomer, nitric oxide, an aquo-complex, a solvate, a metabolite, pharmaceutically acceptable salt or prodrug of the compound as shown in the formula (I). The invention also provides a pharmaceutical composition containing the compound, application of the compound and the pharmaceutical composition in inhibition of HCV (Hepatitis C Virus) copy and HCV virus protein, as well as the application of the compound and the pharmaceutical composition in prevention, handling, treatment or relieving of HCV infection or hepatitis c disease for a patient. The formula I is as shown in the specification.

Bridged Ring compounds As Hepatitis C Virus (HCV) Inhibitors And Pharmaceutical Applications Thereof

Provided herein is a compound having Formula (I), or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or a HCV disorder. Also provided herein are pharmaceutical compositions comprising the compounds disclosed herein, which can be used for treating HCV infection or a HCV disorder.

BRIDGED RING COMPOUNDS AS HEPATITIS C VIRUS (HCV) INHIBITORS AND PHARMACEUTICAL APPLICATIONS THEREOF

Provided herein is a compound having Formula (I), or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or a HCV disorder. Also provided herein are pharmaceutical compositions comprising the compounds disclosed herein, which can be used for treating HCV infection or a HCV disorder.

FUSED RING COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

Provided are fused tricyclic compounds effective to inhibit the function of the NS5A protein of formula (I), wherein X, X', Y, Y', A, A',Q1, Q2, R1-R4, X4, R5a, f and W are defined as in the description. Also provided herein are pharmaceutical compositions thereof, and uses in the manufacture of a medicament for treating HCV infection or a HCV disorder thereof.

SPIRO RING COMPOUND AS HEPATITIS C VIRUS (HCV) INHIBITOR AND USES THEREOF FIELD OF THE INVENTION

A compound of formula (I) or a stereoisomer, a geometric isomer. a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof is provided, which can be used for treating HCV infection or a HCV disorder. Also a pharmaceutical composition comprising the compound and the use of the compound and the pharmaceutical composition thereof are provided, which can also be used for treating HCV infection or a HCV disorder.

Design, synthesis and biological evaluation of hetero-aromatic moieties substituted pyrrole-2-carbonitrile derivatives as dipeptidyl peptidase IV inhibitors

A series of novel hetero-aromatic moieties substituted α-amino pyrrole-2-carbonitrile derivatives was designed and synthesized based on structure-activity relationships (SARs) of pyrrole-2-carbonitrile inhibitors. All compounds demonstrated good dipeptidyl peptidase IV (DPP4) inhibitory activities (IC50 = 0.004-113.6 μM). Moreover, compounds 6h (IC50 = 0.004 μM) and 6n (IC50 = 0.01 μM) showed excellent inhibitory activities against DPP4, good selectivity (compound 6h, selective ratio: DPP8/DPP4 = 450.0; DPP9/DPP4 = 375.0; compound 6n, selective ratio: DPP8/DPP4 = 470.0; DPP9/DPP4 = 750.0) and good efficacy in an oral glucose tolerance test in ICR mice. Furthermore, compounds 6h and 6n demonstrated moderate PK properties (compound 6h, F% = 37.8%, t1/2 = 1.45 h; compound 6n, F% = 16.8%, t1/2 = 3.64 h).

Design, synthesis and biological evaluation of 4-fluoropyrrolidine-2- carbonitrile and octahydrocyclopenta[b]pyrrole-2-carbonitrile derivatives as dipeptidyl peptidase IV inhibitors

Based on the previous work in our group and the principle of computer-aided drug design, a series of novel β-amino pyrrole-2-carbonitrile derivatives was designed and synthesized. Compounds 8l and 9l were efficacious and selective DPP4 inhibitors resulting in decreased blood glucose in vivo. Compound 8l had moderate DPP4 inhibitory activity (IC50 = 0.05 μM) and good oral bioavailability (F = 53.2%). Compound 9l showed excellent DPP4 inhibitory activity (IC50 = 0.01 μM), good selectivity (selective ratio: DPP8/DPP4 = 898.00; DPP9/DPP4 = 566.00) against related peptidases, and good efficacy in an oral glucose tolerance tests in ICR mice and moderate PK profiles (F = 22.8%, t1/2 = 2.74 h). Moreover, compound 9l did not block hERG channel and exhibited no inhibition of liver metabolic enzymes such as CYP2C9.