(5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester

Base Information

• Chemical Name: (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester
• CAS No.: 870097-45-3
• Molecular Formula: C₁₉H₂₃N₃O₆
• Molecular Weight: 389.408

Synonyms:(5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester

Chemical Property of (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester

Chemical Property:

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Technology Process of (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester

There total 6 articles about (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester 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: 13.3%

(R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (870097-43-1) + potassium cyanide + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) → (5R,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (870097-44-2) + (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (870097-45-3)

Guidance literature:

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

DOI:10.1016/j.tetlet.2016.09.032

Reference yield:

(R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (870097-43-1) + potassium cyanide (151-50-8) + ammonium carbonate (506-87-6,6721-33-1,10361-29-2) → (5R,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (870097-44-2) + (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (870097-45-3)

Guidance literature:

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

DOI:10.1021/jo051639u

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester (870097-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydrogencarbonate / water; 1,4-dioxane

2: Jones reagent / acetone / 12 h / Cooling with ice

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

4: water; ethanol / 72 h / Sealed tube

With Jones reagent; sulfuric acid; sodium hydrogencarbonate; In 1,4-dioxane; ethanol; dichloromethane; water; acetone; 4: |Bucherer-Bergs Reaction;

DOI:10.1016/j.tetlet.2016.09.032

upstream raw materials:

(R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

potassium cyanide

ammonium carbonate

4R-4-hydroxyproline

Downstream raw materials:

(3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

C₃₆H₄₈N₁₀O₁₃

C₃₆H₄₈N₁₀O₁₃

C₃₆H₄₈N₁₀O₁₃

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