Process for preparing an N-substitued aldonamide

Details Process for preparing an N-substitued aldonamide Process for preparing an N-substitued aldonamide

1996-06-03

1998-04-21

Kight, John

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 179, 536 187, 536 53, 536124, C07H 100, C07H 1312

Patent

active

057418977

ABSTRACT:
The present invention generally relates to a process for preparing an N-substituted aldonamide by reacting an aldonic acid in a polar organic solvent with an amine of the formula HNR.sup.1 (X--NR.sup.1)nR.sup.2, wherein R1 and R.about. may be the same or different and represent a hydrogen atom, a (cyclo)aliphatic or aromatic hydrocarbon separated by a hetero-atom or not, an amino acid ester, an amino acid amide, an ether amine or an N-alkanoyl alkylene diamine according to the formula R.sup.3 --C(O)N(H)--R.sup.4 --, wherein R.sup.3 =C.sub.1 -C.sub.24 alkyl or alkenyl and R.sup.4 =C.sub.2 -C.sub.22 branched or linear alkylene group, which may contain heteroatoms like N, O, and S, X is a difunctional (cyclo)aliphatic or aromatic hydrocarbon separated or not by a heteroatom or a hydrocarbon substituted hetero-atom, and n=0 or 1, with the proviso that when n=0, R.sup.1 and R.sup.2 do not stand for a hydrogen atom simultaneously, characterised in that an aqueous syrup of the aldonic acid is reacted, optionally after esterification with an alcohol with simultaneous distilling off of the water which is present, at a temperature in the range of 30.degree. to 120.degree. C., with the amine in the organic solvent, which is distilled off wholly or in part simultaneously with any water still present and/or formed.

REFERENCES:
patent: 2746916 (1956-05-01), Magariello et al.
patent: 2752334 (1956-06-01), Walton
patent: 5336765 (1994-08-01), Van et al.
patent: 5386018 (1995-01-01), Au et al.
patent: 5401839 (1995-03-01), Van et al.
patent: 5403922 (1995-04-01), Garelli-Calvet et al.

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