84348-38-9

Basic information

• Product Name: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• Synonyms: 1,2-Pyrrolidinedicarboxylicacid, 4-Methylene-, 1-(1,1-diMethylethyl) ester, (2S)-;(S)-1-(tert-butoxycarbonyl)-4-Methylenepyrrolidine-2-carboxylic acid;N-tert-Butoxycarbonyl-4-methylene-L-proline;N-Boc-4-methylene-L-proline 97%;N-T-BOC-4-METHYLENE-L-PROLINE;(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;BOC-4-METHYLENE-L-PROLINE;N-Boc-4-methylene-L-proline
• CAS NO: 84348-38-9
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• Product Categories: Heterocycles;pharmacetical
• Mol File: 84348-38-9.mol

Chemical Properties

• Melting Point: 110-114°C
• Boiling Point: 349.859 °C at 760 mmHg
• Flash Point: 165.389 °C
• Appearance: /
• Density: 1.18±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.80±0.20(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(84348-38-9)
• EPA Substance Registry System: (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER(84348-38-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 84348-38-9(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is used as a key building block in peptide synthesis, allowing for the creation of complex peptide structures with specific biological activities.
Used in Asymmetric Synthesis:
In asymmetric synthesis, (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is employed as a chiral auxiliary, helping to control the stereochemistry of reactions and produce enantiomerically pure products.
Used in Medicinal Chemistry:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is utilized in medicinal chemistry as a versatile intermediate for the development of novel pharmaceutical compounds, particularly those targeting specific biological receptors or pathways.
Used in Polymer Chemistry:
In the field of polymer chemistry, (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is used as a monomer or building block for the synthesis of functional polymers with tailored properties, such as chiral polymers with specific recognition or binding capabilities.
Used in Fluorous Prolinol Synthesis:
(S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER is used as a starting material for the synthesis of fluorous prolins, which are valuable reagents in organic synthesis and catalysis, offering unique properties due to their fluorous tags.

InChI:InChI=1/C11H17NO4/c1-7-5-8(9(13)14)12(6-7)10(15)16-11(2,3)4/h8H,1,5-6H2,2-4H3,(H,13,14)/t8-/m0/s1

Upstream product

• 163190-46-3 tert-Butyl (2S)-N-tert-butoxycarbonyl-4-methylideneprolinate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 144423-03-0 N-phenylsulphonyl-N-propargyl-O-tetrahydropyranyl-(S)-serine benzylester 
• 144422-80-0 N-phenylsulphonyl-N-propargyl-3-bromo-(S)-alanine benzylester 
• 144422-81-1 N-phenylsulphonyl-4-exomethylene-(S)-proline benzylester 
• 84348-39-0 (S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate 
• 20309-87-9 (2S)-4-methylenepyrrolidine-2-carboxylic acid 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 27200-84-6 methyl triphenylphosphonium bromide 

Downstream Products

• 1129634-43-0 (6S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate 
• 84348-39-0 (S)-1-tert-butyl 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate 
• 1129634-44-1 (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid 
• 1499193-61-1 (S)-6-(2-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-oxoethyl) 5-tert-butyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate 
• 1441670-89-8 (6S)-6-[5-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]heptane-5-carboxylic acid 1,1-dimethylethyl ester 
• 1343476-08-3 (S)-(4,4‘-(pentane-1,5-diylbis(oxy))bis(5-methoxy-2-nitro-4,1-phenylene))bis(((S)-2-(methoxycarbonyl)-4-methylenepyrrolidin-1-yl)methanone) 

Relevant articles and documents

MASP INHIBITORY COMPOUNDS AND USES THEREOF

The present invention relates to novel Mannose-binding lectin (MBL)-associated serine protease (MASP) inhibitory compounds, as well as analogues and derivatives thereof, to processes for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of renal and cardiovascular disorders and of ischemia reperfusion injuries.

An enantioselective approach to 4-substituted proline scaffolds: Synthesis of (s)-5-(tert-butoxy carbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid

A catalytic and enantioselective preparation of the (S)-4-methyleneproline scaffold is described. The key reaction is a one-pot double allylic alkylation of an imine analogue of glycine in the presence of a chinchonidine-derived catalyst under phase transfer conditions. These 4-methylene substituted proline derivatives are versatile starting materials often used in medicinal chemistry. In particular, we have transformed tert-butyl (S)-4-methyleneprolinate (12) into the N-Boc-protected 5-azaspiro[2.4]heptane-6-carboxylic acid (1), a key element in the industrial synthesis of antiviral ledipasvir.

Ledipasvir preparation method

The invention discloses a Ledipasvir preparation method. The Ledipasvir preparation method includes steps: (1) Ledipasvir intermediate product 1-LD-B preparation; (2) Ledipasvir intermediate product 2-LD-E preparation; (3) Ledipasvir intermediate product 3-LD-F preparation; (4) Ledipasvir intermediate product 4-LD-J preparation; (5) Ledipasvir intermediate product 5-LD-L preparation; (6) Ledipasvir-LD-Q preparation. The Ledipasvir preparation method has advantages of technical maturity and stability, product quality stability, safety and reliability in production process and suitableness for industrial production.

ARYL, HETEROARYL, AND HETEROCYCLIC COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement Factor D comprising Formula I, or a pharmaceutically acceptable salt or composition thereof wherein R12 or R13 on the A group is an aryl, heteroaryl or heterocycle (R32) are provided. The inhibitors of Factor D described herein reduce the excessive activation of complement.

DIHYDROPYRIMIDINE COMPOUNDS AND THEIR APPLICATION IN PHARMACEUTICALS

Provided herein are dihydropyrimidine compounds and their pharmaceutical applications, especially for use in treating and preventing HBV diseases. Specifically, provided herein are compounds having Formula (I) or (Ia), or an enantiomer, a diastereoisomer,

PROCESSES FOR THE PREPARATION OF 5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID AND ITS DERIVATIVES

The present invention relates generally to an improved process for the preparation of 5-azaspiro[2.4]heptane-6-carboxylic acid and its derivatives which are useful intermediates in the synthesis of biologically active molecules, especially in the synthesis of hepatits C virus NS5A inhibitors. In particular, the present invention relates to processes and intermediates for the preparation of compounds of formulae (la), (lb) and (Ic):

PYRROLOBENZODIAZEPINES

The invention relates to certain pyrrolobenzodiazepines (PBDs), and in particular pyrrolobenzodiazepine dimers bearing C2 substitutions, including compounds of formula (T): wherein: R2 is CHR2A, and R2A is independently selected from H, R, CO2R, COR, CHO, CO2H, and halo; R6 and R9 are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR', NO2, Me3Sn and halo; R7 is independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR', NO2, Me3Sn and halo; R8 is independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR', NO2, Me3Sn and halo; R is independently selected from optionally substituted C1-12 alkyl, C3-20 heterocyclyl and C5-20 aryl groups; or the compound is a dimer with each monomer being of formula (M), where the R7 groups or R8 groups of each monomer form together a dimer bridge having the formula -X-R"-X- linking the monomers; wherein R" is a C3-I2 alkylene group, which chain may be interrupted by one or more heteroatoms, e.g. O, S, N(H), and/or aromatic rings, e.g. benzene or pyridine; and each X is independently selected from O, S, or N(H); or any pair of adjacent groups from R6 to R9 together form a group -O-(CH2)P-O-, where p is 1 or 2, and salts and solvates thereof, and their use as intermediates for the preparation of other PBD compounds.

Inhibitors of Serine Proteases

The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention.

INHIBITORS OF SERINE PROTEASES FOR THE TREATMENT OF HCV INFECTIONS

The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt thereof. These compounds inhibit serine protease, particularly the hepatitis C virus NS3-NS4A protease.

INHIBITORS OF SERINE PROTEASES

The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt or mixtures thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.