Process for preparing glycopeptide derivatives
View Patent ↗Disclosed are processes for preparing glycopeptide antibiotic derivatives having an amino-containing side chain. The multi-step process is conducted in a single reaction vessel without isolation of intermediate reaction products.
1. A process for preparing a compound of formula I:
or a salt thereof; the process comprising:
(a) forming a reaction mixture comprising vancomycin or a salt thereof, and a compound of formula II:
(b) contacting the reaction mixture from step (a) with a tertiary amine;
(c) contacting the reaction mixture from step (b) with an acid;
(d) contacting the reaction mixture from step (c) with a reducing agent;
(e) contacting the reaction mixture from step (d) with an amine; to provide a compound of formula I or a salt thereof.
2. The process of claim 1 , wherein the vancomycin employed in step (a) is a hydrochloride salt.
3. The process of claim 1 , wherein the tertiary amine employed in step (b) is diisopropylethylamine.
4. The process of claim 1 , wherein the acid employed in step (c) is trifluoroacetic acid.
5. The process of claim 1 , wherein the reducing agent employed in step (d) is tert-butylamine/borane.
6. The process of claim 1 , wherein the amine employed in step (e) is tert-butylamine.
7. A process for preparing a compound of formula I:
or a salt thereof; the process comprising:
(a) forming a reaction mixture comprising vancomycin hydrochloride, and a compound of formula II:
(b) contacting the reaction mixture from step (a) with diisopropylamine;
(c) contacting the reaction mixture from step (b) with trifluoroacetic acid;
(d) contacting the reaction mixture from step (c) with tert-butylamine/borane;
(e) contacting the reaction mixture from step (d) with tert-butylamine; to provide a compound of formula I or a salt thereof.