(S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester

Base Information

• Chemical Name: (S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester
• CAS No.: 204187-32-6
• Molecular Formula: C₂₉H₂₆N₂O₈
• Molecular Weight: 530.534

Synonyms:

Chemical Property of (S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester

There total 2 articles about (S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl) 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:

endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide (21715-90-2,397299-61-5) + (2S)-benzylsuccinic acid (3972-36-9,884-33-3) → (S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester (204187-32-6)

Guidance literature:

With thionyl chloride; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, RT, overnight;

DOI:10.1248/cpb.46.337

Reference yield:

2-benzylsuccinic acid (36092-42-9,884-33-3) → (S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester (204187-32-6)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) SOCl₂, Et₃N / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, RT, overnight

With thionyl chloride; triethylamine;

DOI:10.1248/cpb.46.337

Reference yield:

(S)-2-Benzyl-succinic acid 4-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester 1-((1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl) ester (204187-32-6) → mitiglinide (145375-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 0 - 20 °C

2: 90 percent / 2N NaOH / methanol / 15 h / Ambient temperature

With sodium hydroxide; In methanol; dichloromethane;

DOI:10.1248/cpb.46.337

upstream raw materials:

endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide

(2S)-benzylsuccinic acid

2-benzylsuccinic acid

Downstream raw materials:

(S)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid (1R,2S,6R,7S)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester

mitiglinide

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