Process for preparing o-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides
US6180787A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Dec 15, 1999 |
| Grant date | Jan 30, 2001 |
| Priority date | — |
| Expiry date | Dec 15, 2019 |
Classification
- Technology area (CPC A)Human Necessities
- CPC primaryA61P3/10
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention relates to a novel process for preparing O-(3-amino-2-hydroxy-propyl)-hydroxymic acid halides of formula (I) by reacting a carboxamide oxime of formula (II) wherein R.sup.1 is as specified above with reactive 3-amino-2-hydroxy-propane derivative diazotizing the O-substituted carboxamide oxime thus obtained with sodium nitrite in the presence of hydrogen halide, decomposing the diazonium salt and if desired, separating the optically active enantiomers and/or reacting the resulting base with an organic or mineral acid wherein the carboxamide oxime of formula (II) is reacted with a 3-hydroxy azetidinium salt of formula (III) wherein R.sup.2 and R.sup.3 are a defined above and Y.sup.- is a salt forming anion, in a lower alcoholic, preferably ethanolic medium optionally containing water and made alkaline with an alkali hydroxide, and before diazotizing the O-substituted carboxamide oxime intermediate obtained, the reaction mixture is neutralised and the organic solvent is removed. The process according to the invention provides the compounds of formula (I) with higher yield compared to the prior art processes.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.