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
• Article Data: 31

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

Chemical Properties

White powder

Uses

N-Boc-cis-4-fluoro-L-proline can be used as a substrate in the preparation of:α4β2 Receptor ligands bearing pyrrolidine nucleus.β-Amino pyrrolidine-2-carbonitrile derivatives as possible dipeptidyl peptidase IV (DPP4) inhibitors.

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

• 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 
• 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 
• 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 
• 441714-17-6 ethyl 1-[1-(tert-butoxycarbonyl)-(4S)-fluoro-(2S)-pyrrolidinylcarbonyl]-4-piperidinylacetate 
• 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 
• 426844-23-7 (2S,4S)-4-fluoropyrrolidine-2-carboxamide hydrochloride 
• 886447-52-5 ethyl [4-[(4S)-fluoro-1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]acetate 
• 317356-29-9 4-((2S,4S)-4-Fluoro-1-{2-[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetyl}-pyrrolidin-2-ylmethoxy)-benzoic acid methyl ester 
• 317356-28-8 methyl 4-[1-(tert-butoxycarbonyl)-(4S)-fluoro-(2S)-pyrrolidinyl]methoxybenzoate 
• 315710-15-7 methyl 4-[(2S,4S)-4-fluoropyrrolidin-2-ylmethoxy]benzoate 

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.

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.

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.