(S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID

Base Information

• Chemical Name: (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID
• CAS No.: 1129634-44-1
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.287
• Hs Code.: 2933990090
• Mol file: 1129634-44-1.mol

Synonyms:(S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID;5-Azaspiro[2.4]heptane-5,6-dicarboxylic acid, 5-(1,1-diMethylethyl) ester, (6S)-;(S)-5-(tert-Butoxycarbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid;Ledipasvir side chain

Chemical Property of (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID

Chemical Property:

• Boiling Point: 377.4±35.0 °C(Predicted)
• PKA: 4.04±0.20(Predicted)
• PSA: 66.84000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 1.79850
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(S)-5-Boc-5-azaspiro[2.4]heptane-6-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID is a key intermediate in the synthesis of ledipasvir, an antiviral NS5A inhibitor. It is derived from (S)-4-methyleneproline scaffolds through catalytic enantioselective synthesis and subsequent transformations, including electrochemical dehalogenation for industrial-scale production. (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID features a spirocyclic structure with a Boc-protected azaspiroheptane core and a carboxylic acid functionality, making it a versatile building block in medicinal chemistry.

Technology Process of (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID

There total 52 articles about (S)-5-BOC-5-AZASPIRO[2.4]HEPTANE-6-CARBOXYLIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(6S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate (1129634-43-0) → (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid (1129634-44-1,1454843-77-6,1454843-78-7)

Guidance literature:

(6S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate; With lithium hydroxide monohydrate; water; In ethanol; at 20 ℃; for 20h;

With hydrogenchloride; In water; pH=2; Ice bath;

Reference yield: 100.0%

(6S)-5-(tert-butoxycarbonyl)-5-azaspiro[2.4]heptane-6-carboxylic acid R-α-methylbenzylamine salt → (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid (1129634-44-1,1454843-77-6,1454843-78-7)

Guidance literature:

With hydrogenchloride; In Isopropyl acetate; water; at 0 ℃; pH=3 - 4;

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-5-azaspiro[2.4]heptane-6-carboxylic acid D-di-p-methylbenzoyltartrate → (6S)-5-[(tert-butoxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acid (1129634-44-1,1454843-77-6,1454843-78-7)

Guidance literature:

(S)-5-azaspiro[2.4]heptane-6-carboxylic acid D-di-p-methylbenzoyltartrate; With hydrogenchloride; In dichloromethane; water; for 0.333333h; pH=2-3;

di-tert-butyl dicarbonate; With sodium hydroxide; In dichloromethane; water; at 0 - 50 ℃; pH=10-11;

upstream raw materials:

(6S)-5-tert-butyl 6-methyl 5-azaspiro[2.4]heptane-5,6-dicarboxylate

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Downstream raw materials:

(S)-tert-butyl 6-(5-(4-iodophenyl)-1H-imidazol-2-yl)-5-azaspiro[2.4]heptane-5-carboxylate

C₂₃H₃₃N₃O₃Si

C₂₀H₂₄INO₅

(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

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