1454843-77-6

Basic information

• Product Name: 5-Azaspiro[2.4]heptane-5,6-dicarboxylic acid, 5-(1,1-dimethylethyl) ester
• Synonyms: 5-Azaspiro[2.4]heptane-5,6-dicarboxylic acid, 5-(1,1-dimethylethyl) ester
• CAS NO: 1454843-77-6
• Molecular Weight: 0
• Mol File: 1454843-77-6.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 5-Azaspiro[2.4]heptane-5,6-dicarboxylic acid, 5-(1,1-dimethylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Azaspiro[2.4]heptane-5,6-dicarboxylic acid, 5-(1,1-dimethylethyl) ester(1454843-77-6)
• EPA Substance Registry System: 5-Azaspiro[2.4]heptane-5,6-dicarboxylic acid, 5-(1,1-dimethylethyl) ester(1454843-77-6)

Safety Data

• Hazardous Substances Data: 1454843-77-6(Hazardous Substances Data)

Upstream product

• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 958275-39-3 (3R,7aS)-6-methylene-3-phenyltetrahydropyrrolo[1,2-c]oxazol-5(1H)-one 
• 1431322-84-7 (3’R,7a’S)-3’-phenyldihydro-1‘H-spiro[cyclopropane-1,6’-pyrrolo[1,2-c][1,3]oxazol]-5’-one 
• 1431322-85-8 ((S)-(5-benzyl-5-azaspiro[2.4]heptan-6-yl)methanol) 
• 1412903-77-5 (6S)-1,1-dibromo-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid 
• 163190-46-3 tert-Butyl (2S)-N-tert-butoxycarbonyl-4-methylideneprolinate 
• 1026796-26-8 tert-butyl 5-azaspiro[2.4]heptane-5-carboxylate 
• 68-12-2 N,N-dimethyl-formamide 
• 1454843-77-6 (±)-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid 
• 14719-37-0 ethyl 2-(tert-butoxycarbonylamino)acetate 
• 136476-38-5 cyclopropane-1,1-diylbis(methylene) dimethanesulfonate 
• 83321-23-7 1,1-bis(iodomethyl)cyclopropane 
• 39590-81-3 [1-(hydroxymethyl)cyclopropyl]methanol 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1430105-00-2 (S)-tert-butyl 6-(5-(4-iodophenyl)-1H-imidazol-2-yl)-5-azaspiro[2.4]heptane-5-carboxylate 
• 1431322-88-1 C₂₃H₃₃N₃O₃Si 
• 1430104-98-5 C₂₀H₂₄INO₅ 
• 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 
• 1129634-44-1 (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid 
• 1262397-14-7 (S)-tert-butyl 6-formyl-5-azaspiro[2.4]heptane-5-carboxylate 
• 1454843-77-6 (R)-5-Boc-azaspiro[2.4]heptane-6 carboxylic acid 

Relevant articles and documents

Development of potent and selective Cathepsin C inhibitors free of aortic binding liability by application of a conformational restriction strategy

Cathepsin C plays a key role in the activation of several degradative enzymes linked to tissue destruction in chronic inflammatory and autoimmune diseases. Therefore, Cathepsin C inhibitors could potentially be effective therapeutics for the treatment of diseases such as chronic obstructive pulmonary disease (COPD) or acute respiratory distress syndrome (ARDS). In our efforts towards the development of a novel series of Cathepsin C inhibitors, we started working around AZD5248 (1), an α-amino acid based scaffold having potential liability of aortic binding. A novel series of amidoacetonitrile based Cathepsin C inhibitors were developed by the application of a conformational restriction strategy on 1. In particular, this work led to the development of a potent and selective Cathepsin C inhibitor 3p, free of aortic binding liability.

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.