Process for the preparation of advantame
AssigneeDivi's Laboratories, Ltd.
InventorsMurali Krishna Prasad Divi, Mysore Aswatha Narayana Rao, Shaik Nowshuddin
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Abstract
A novelprocess for the preparation of N—[N-[3-(3-hydroxy-4-methoxyphenyl)-propyl]-L-α-aspartyl]-L-phenylalanine-1-methyl ester is described. It comprises, reacting isovanillin or its derivative with vinyl acetate followed by reductive condensation with L-[α-aspartyl]-L-phenylalanine-1-methyl ester.
Claims4
A process for the preparation of N—[N-[3-(3-hydroxy-4-methoxyphenyl)-propyl]-α-aspartyl]-L-phenylalanine-1-methyl ester (Advantame) comprising:
- condensing isovanillin or O-benzylisovanillin having the following structure:
- with vinyl acetate having the structure:
- in aqueous alkaline medium to obtain (3-hydroxy-4-methoxy) cinnamaldehyde (II) or its derivative (IIa) having the structure:
- Condensing (3-hydroxy-4-methoxy) cinnamaldehyde (II) or its derivative (IIa) with Aspartame having the structure:
- through reductive amination to obtain a phenylpropenyl derivative of Aspartame (V or Vb) having the structure:
- and subjecting (V) or (Vb) to catalytic hydrogenation.
A process according to claim-1, wherein condensation of isovanillin or O-benzylisovanillin with vinyl acetate is carried out at a temperature range of −15° to 0° C.
A process according to claim-1, wherein condensing (4-methoxy-3-hydroxy)cinnamaldehyde
- (II) or its derivative (IIa) with Aspartame through reductive amination is carried out using sodium borohydride and acetic acid.
A process for the preparation of (3-hydroxy-4-methoxy) cinnamaldehyde (II) or its derivative (IIa) by condensing isovanillin or O-benzylisovanillin with vinyl acetate in aqueous alkaline medium.
Dependencies are inferred from the claim text.