72180-14-4

Basic information

• Product Name: （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo
• Synonyms: （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo;（2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarboxylate;(2S,4S)-1-benzyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate;(2S,4S)-4-fluoro-1,2-Pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester;(2S,4S)-1-(Benzyloxycarbonyl)-2-(methoxycarbonyl)-4-fluoropyrrolidine
• CAS NO: 72180-14-4
• Molecular Formula: C₁₄H₁₆FNO₄
• Molecular Weight: 281.281
• Mol File: 72180-14-4.mol

Chemical Properties

• Boiling Point: 382.901 °C at 760 mmHg
• Flash Point: 185.372 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: 2-8°C
• PKA: -5.73±0.60(Predicted)
• CAS DataBase Reference: （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo(CAS DataBase Reference)
• NIST Chemistry Reference: （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo(72180-14-4)
• EPA Substance Registry System: （2s，4s）-1-benzyl-2-methy-4-fluoropyrrolidine-1，2-dicarbo(72180-14-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 72180-14-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-1-benzyl-2-methyl-4-fluoropyrrolidine-1,2-dicarboxylate is used as a potential central nervous system stimulant for its ability to potentially enhance cognitive function and alertness.
(2S,4S)-1-benzyl-2-methyl-4-fluoropyrrolidine-1,2-dicarboxylate is used as a potential psychoactive substance for its potential to induce changes in mood, perception, or consciousness.
(2S,4S)-1-benzyl-2-methyl-4-fluoropyrrolidine-1,2-dicarboxylate is used as a potential anesthetic for its potential ability to induce a temporary loss of sensation or pain.
(2S,4S)-1-benzyl-2-methyl-4-fluoropyrrolidine-1,2-dicarboxylate is used as a potential analgesic for its potential to relieve pain.
Note: The uses mentioned above are based on the potential applications of (2S,4S)-1-benzyl-2-methyl-4-fluoropyrrolidine-1,2-dicarboxylate, as its specific pharmacological properties are still under investigation. Further research is required to confirm its efficacy and safety in these applications.

InChI:InChI=1/C14H16FNO4/c1-19-13(17)12-7-11(15)8-16(12)14(18)20-9-10-5-3-2-4-6-10/h2-6,11-12H,7-9H2,1H3/t11-,12-/m0/s1

Upstream product

• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 67-56-1 methanol 
• 1235447-42-3 (2S,4S)-N-Cbz-4-fluoropyrrolidine-2-carbonyl fluoride 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 72204-21-8 N-benzyloxycarbonyl-(4S)-fluoro-L-proline 
• 185212-86-6 N-benzyloxycarbonyl-(4S)-fluoro-L-proline n-butylamide 
• 203866-16-4 1-tert-butyl 2-methyl (2S,4S)-4-fluoropyrrolidine-1,2-dicarboxylate 
• 1358943-62-0 C₁₃H₁₄FNO₃ 
• 1358946-07-2 C₁₉H₂₂FN₃ 
• 1358945-94-4 C₂₁H₂₆FN₃ 
• 203866-13-1 (2S,4S)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid 

Relevant articles and documents

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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.

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4-fluoropyrrolidine-2-carbonyl fluorides: Useful synthons and their facile preparation with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride

4-Fluoropyrrolidine derivatives are useful in medicinal chemistry applications such as dipeptidyl peptidase IV inhibitors. As attractive synthons for these, N-protected (2S,4S)-4-fluoropyrrolidine-2-carbonyl fluorides were synthesized in high yield by double fluorination of N-protected (2S,4R)-4-hydroxyproline with 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (Fluolead). The 4-fluoropyrrolidine-2-carbonyl fluorides were converted to useful intermediates such as 4-fluoropyrrolidine-2-carboxamides, -N-methoxy-N-methylcarboxamide (Weinreb amide), -carboxylate methyl esters, and -carbonitriles in excellent yields. The crystalline N-Fmoc-cis-4- fluoropyrrolidine-2-carbonyl fluoride 2a is a particularly useful synthon due to its high yield of preparation and easy isolation as an enantiomerically pure compound by crystallization. Thus, the methodology using the synthons prepared by the stereospecific double fluorination has enabled a significant decrease in the synthetic steps needed for the preparation of the 4-fluoropyrrolidine derivatives useful for medicinal applications.

NOVEL 4-FLUOROPYRROLIDINE-2-CARBONYL FLUORIDE COMPOUNDS AND THEIR PREPARATIVE METHODS

Novel 4-fluoropyrrolidine-2-carbonyl fluoride compounds as useful fluorinated intermediates are disclosed. Their preparative methods are also disclosed. Useful applications of the 4-fluoropyrrolidine-2-carbonyl fluorides are shown.

Discovery and synthesis of HIV integrase inhibitors: Development of potent and orally bioavailable N-methyl pyrimidones

The human immunodeficiency virus type-1 (HIV-1) encodes three enzymes essential for viral replication: a reverse transcriptase, a protease, and an integrase. The latter is responsible for the integration of the viral genome into the human genome and, therefore, represents an attractive target for chemotherapeutic intervention against AIDS. A drug based on this mechanism has not yet been approved. Benzyl-dihydroxypyrimidine-carboxamides were discovered in our laboratories as a novel and metabolically stable class of agents that exhibits potent inhibition of the HIV integrase strand transfer step. Further efforts led to very potent compounds based on the structurally related N-Me pyrimidone scaffold. One of the more interesting compounds in this series is the 2-N-Me-morpholino derivative 27a, which shows a CIC95 of 65 nM in the cell in the presence of serum. The compound has favorable pharmacokinetic properties in three preclinical species and shows no liabilities in several counterscreening assays.

PROCESS FOR PRODUCTION OF CIS-4-FLUORO-L-PROLINE DERIVATIVES

The present invention provides a safer method for production of a cis-4-fluoro-L-proline derivative under milder conditions and in good yield to give a product of high purity on an industrial scale at low cost. Namely, the present invention provides a method for producing a cis-4-fluoro-L-proline derivative, which comprises reacting a trans-4-hydroxy-L-proline derivative of the following Formula [I]: (wherein R1 represents a protecting group for an α-amino group, and R2 represents a protecting group for a carboxyl group) with N,N-diethyl-N-(1,1,2,3,3,3-hexafluoropropyl)amine in the presence of a hydrogen fluoride-scavenger.

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