1,3,7-Triazaspiro[4.4]nonane-7,8-dicarboxylic acid, 2,4-dioxo-, 8-(1,1-dimethylethyl) 7-(phenylmethyl) ester, (5S,8S)-

Base Information

• Chemical Name: 1,3,7-Triazaspiro[4.4]nonane-7,8-dicarboxylic acid, 2,4-dioxo-, 8-(1,1-dimethylethyl) 7-(phenylmethyl) ester, (5S,8S)-
• CAS No.: 526222-96-8
• Molecular Formula: C19H23N3O6
• Molecular Weight: 389.408
• Mol file: 526222-96-8.mol

Synonyms:

Chemical Property of 1,3,7-Triazaspiro[4.4]nonane-7,8-dicarboxylic acid, 2,4-dioxo-, 8-(1,1-dimethylethyl) 7-(phenylmethyl) ester, (5S,8S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,7-Triazaspiro[4.4]nonane-7,8-dicarboxylic acid, 2,4-dioxo-, 8-(1,1-dimethylethyl) 7-(phenylmethyl) ester, (5S,8S)-

There total 7 articles about 1,3,7-Triazaspiro[4.4]nonane-7,8-dicarboxylic acid, 2,4-dioxo-, 8-(1,1-dimethylethyl) 7-(phenylmethyl) ester, (5S,8S)- 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: 50.5%

potassium cyanide + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) + (2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester (147489-27-8) → (5R,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (526222-97-9) + (5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (526222-96-8)

Guidance literature:

In ethanol; water; for 72h; Sealed tube;

DOI:10.1016/j.tetlet.2016.09.032

Reference yield:

1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9) → (5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (526222-96-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / dichloromethane / 12 h / Cooling with ice

2: water; ethanol / 72 h / Sealed tube

With sulfuric acid; In ethanol; dichloromethane; water; 2: |Bucherer-Bergs Reaction;

DOI:10.1016/j.tetlet.2016.09.032

Reference yield:

potassium cyanide (151-50-8) + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) + (2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester (147489-27-8) → (5R,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (526222-97-9) + (5S,8S)-2,4-dioxo-1,3,7-triazaspiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (526222-96-8)

Guidance literature:

In water; N,N-dimethyl-formamide; at 60 ℃; for 4h;

DOI:10.1021/ja0293958

upstream raw materials:

potassium cyanide

ammonium carbonate

(2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester

4R-4-hydroxyproline