85665-59-4

Basic information

• Product Name: methyl 1-(chlorocarbonyl)-L-prolinate
• Synonyms: methyl 1-(chlorocarbonyl)-L-prolinate;1-(Chlorocarbonyl)-L-proline methyl ester;1-(Chlorocarbonyl)-L-Pro-OMe;Einecs 288-148-4
• CAS NO: 85665-59-4
• Molecular Formula: C₇H₁₀ClNO₃
• Molecular Weight: 191.6122
• EINECS: 288-148-4
• Mol File: 85665-59-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 1-(chlorocarbonyl)-L-prolinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-(chlorocarbonyl)-L-prolinate(85665-59-4)
• EPA Substance Registry System: methyl 1-(chlorocarbonyl)-L-prolinate(85665-59-4)

Safety Data

• Hazardous Substances Data: 85665-59-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H10ClNO3/c1-12-6(10)5-3-2-4-9(5)7(8)11/h5H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 75-44-5 phosgene 
• 4931-66-2 methyl (S)-pyroglutamate 
• 147-85-3 L-proline 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 43041-12-9 methyl pyrrolidine-2-carboxylate 
• 2133-40-6 methyl pyrrolidine-2-carboxylate hydrochloride 
• 103322-13-0 L-1-(chlorocarbonyl)-4,5-dihydroproline methyl ester 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 128252-48-2 (-)-(S)-methyl 1-<<(benzyloxy)amino>carbonyl>pyrrolidine-2-carboxylate 
• 946438-16-0 methyl 1-(3-phenylpropanoyl)pyrrolidine-2-carboxylate 
• 1187819-31-3 (S)-1-(4-chloro-2-((2-chloro-4-nitrophenyl)carbamoyl)phenyl) 2-methyl pyrrolidine-1,2-dicarboxylate 
• 147-85-3 L-proline 
• 140160-63-0 (5S)-3-hydroxy-1,3-diazabicyclo<3.3.0>octane-2,4-dione 
• 140160-62-9 (5S)-3-(benzyloxy)-1,3-diazabicyclo<3.3.0>octane-2,4-dione 

Relevant articles and documents

Design, synthesis and anti-inflammatory effects of novel 9-O-substituted-berberine derivatives

Berberine, an isoquinoline alkaloid in many medicinal herbs, has been found to possess broad pharmacological activities. A series of novel C-9-O-substituted-berberine derivatives have been synthesized and their anti-inflammatory effects evaluated both in vitro and in vivo. Compared to berberine, the new synthetic berberine derivatives 3i and 5e exhibit significantly improved inhibitory activities against the release of NO, TNF-α and IL-6. Furthermore, derivatives 3i and 5e were found to inhibit more effectively the migration of neutrophils and primitive macrophage in transgenic zebrafish larvae with injury-provoked inflammation. Pre-treatment with derivatives 3i or 5e could lead to a concentration-dependent decrease in nuclear factor-κB (NF-κB) p65 and NF-κB inhibitor α (IκBα) phosphorylation and inducible nitric oxide synthase (iNOS) expression in lipopolysaccharide (LPS)-induced RAW264.7 cells, which suggested that the anti-inflammatory activities of berberine derivatives 3i and 5e are related to their suppression of the NF-κB signal pathway.

Glutamate receptor modulators and therapeutic agents

The present invention discloses methods of modulating the activity of Group I mGluRs using a defined class of benzamide compounds. In one embodiment, methods of modulating the activity of mGluR1 are provided. In another embodiment, methods of modulating the activity of mGluR5 are provided. In still another embodiment, methods of simultaneously modulating the activities of both mGluR1 and mGluR5 are provided. The present invention also provides methods of treating diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of benzamide compounds. The present invention further provides methods of preventing diseases or disorders which are mediated in full or in part by Group I mGluRs using one or more compounds belonging to the defined class of compounds. Diseases and disorders contemplated include, inter alia, diseases and disorders of the central nervous system, the peripheral nervous system, the gastrointestinal system, the circulatory system, skin, retina, brain, heart, and lungs.

Amino Acids. 7. A Novel Synthetic Route to L-Proline

Reaction of L-5-oxoproline esters L-2 with phosgene at 0 deg C gives L-5,5-dichloro-1-(chlorocarbonyl)proline esters L-6, which readily lose hydrogen chloride to form L-5-chloro-1-(chlorocarbonyl)-4,5-dehydroproline esters L-7.Catalytic hydrogenation (Pd/C, 180 bar) of L-7 yields L-1-(chlorocarbonyl)proline esters L-15 and thence, upon hydrolysis, L-proline (L-17).A 'one-pot reaction' for the whole sequence is described, starting from easily accessible L-5-oxoproline esters and yielding L-proline in 78percent overall yield and 99.7percent optical purity.