204187-32-6

Basic information

• Product 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 Weight: 530.534
• Mol File: 204187-32-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (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 DataBase Reference)
• NIST Chemistry Reference: (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(204187-32-6)
• EPA Substance Registry System: (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(204187-32-6)

Safety Data

• Hazardous Substances Data: 204187-32-6(Hazardous Substances Data)

Upstream product

• 21715-90-2 endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide 
• 3972-36-9 (2S)-benzylsuccinic acid 
• 36092-42-9 2-benzylsuccinic acid 

Downstream Products

• 145375-43-5 mitiglinide 
• 204187-36-0 (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 

Relevant articles and documents

Preparation of optically active succinic acid derivatives. II. Efficient and practical synthesis of KAD-1229

For large-scale synthesis of monocalcium bis[(2s)-2-benzyl-3-(cis- hexahydroisoindolin-2-ylcarbonyl)propionate]dihydrate (1, KAD-1229), we investigated regioselective reactions of (S)-2-benzylsuccinic acid (2) with cis-hexahydroisoindoline (4). It was difficult to obtain a half amide regioselectively through coupling reaction of the (S)-acid 2 with the amine 4. Therefore, the succinic acid 2 was converted to bis-activated esters 3a-c and these were reacted with 4 to give the amides 5a-c in good yields, regioselectively. The amides 5a-c were derived to KAD-1229, which has a potent hypoglycemic effect, in good yields.