Selective N-acylation of amino alcohols
AssigneeGist-Brocades N.V.
InventorsJan W. H. Smeets, Pieter G. Weber
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Abstract
The present invention provides an efficient method for the production of N-acyl amino alcohols via the selective acylation of the free amines of amino alcohols by reacting with an organic acid or a salt thereof with an alkyl sulfonyl chloride or an alkyl phenyl sulfonyl chloride, in an organic solvent and in the presence of an organic base, to form the corresponding mixed anhydride, followed by reacting the mixed anhydride with an amino alcohol or a salt thereof to form the corresponding N-acyl amino alcohol.
Claims23
A method for the production of N-acyl amino alcohols which is characterized by:
- reacting an organic acid (or a salt thereof) of the formula:
- R--COOH
- wherein
- R is a straight chain or branched alkyl group having up to 55 carbon atoms, wherein the alkyl chain may optionally be interrupted by an oxygen atom or by an internal ester group;
- may optionally contain one or more double bonds;
- and may optionally be substituted with one or more protected hydroxyl moieties,
- with a C.sub.1-6 alkyl sulfonyl chloride or a C.sub.1-6 alkyl phenyl sulfonyl chloride, in an organic solvent and in the presence of an organic base, to form the corresponding mixed anhydride having the formula:
- R--CO--O--SO.sub.2 R'"
- wherein
- R is as defined above;
- and
- R'" is a C.sub.1-6 alkyl or a C.sub.1-6 alkyl phenyl group;
- and
- reacting, in an organic solvent, the mixed anhydride with an amino alcohol or a salt thereof to form the corresponding N-acyl amino alcohol.
A method for the production of N-acyl amino alcohols which is characterized by:
- reacting, in an organic solvent, a mixed anhydride having the formula:
- R--CO--O--SO.sub.2 R'"
- wherein
- R is a straight chain or branched alkyl group having up to 55 carbon atoms, herein the alkyl chain may optionally be interrupted by an oxygen atom or by an internal ester group;
- may optionally contain one or more double bonds;
- and may optionally be substituted with one or more protected hydroxyl moieties;
- and
- R'" is a C.sub.1-6 alkyl or a C.sub.1-6 alkyl phenyl group,
- with an amino alcohol or a salt thereof to form the corresponding N-acyl amino alcohol.
Dependencies are inferred from the claim text.