787635-23-8

Upstream product

• 94594-90-8 (2R)-bornane-10,2-sultam 
• 645-45-4 hydrocinnamic acid chloride 
• 127392-81-8 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one 
• 787635-22-7 1,1-dimethylethyl (3S)-4-[(3aS,6R,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-4-oxo-3-(phenylmethyl)butanoate 

Downstream Products

• 787635-24-9 (3aS,6R,7aS)-8,8-dimethyl-1-{(2S)-4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-(phenylmethyl)butanoyl}hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 145375-43-5 mitiglinide 
• 3972-36-9 (2S)-benzylsuccinic acid 

Relevant academic research and scientific papers

A practical and efficient preparation of (S)-2-benzylsuccinic acid: A key acid synthon of KAD-1229

This report describes a practical and an efficient synthesis of (S)-2-benzyl-succinic acid, which was employed as a key intermediate for hypoglycemic KAD-1229 by means of asymmetric alkylation of N-acylsultam. The condensation of D-(-)-camphorsultam with 3-phenylpropionyl chloride gave N-acylsultam 1. N-acylsultam 1 reacted with 1.1 equimolar amount of sodium amide base to form chiral enolate, followed by alkylation with tert-butyl bromoacetate to afford 2. Cleavage of ester and saponification with H 2O2-LiOH provided the desired compound 5 with excellent yield and high optical purity.

An effective and convenient method for the preparation of KAD-1229

A new convenient method for the asymmetric synthesis of the potent hypoglycemic agent KAD-1229 was developed. The key step of this method is diasteroselective alkylation of 1 to give crude 2 (d.e. > 93%) in good yield with the easily available Oppolzer's