157060-06-5

Upstream product

• 100-02-7 4-nitro-phenol 
• 3972-36-9 (2S)-benzylsuccinic acid 
• 36092-42-9 2-benzylsuccinic acid 

Downstream Products

• 204187-34-8 (S)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid 4-nitro-phenyl ester 
• 204187-39-3 (S)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid methyl ester 
• 145375-43-5 mitiglinide 

Relevant academic research and scientific papers

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.