We describe a new synthesis of the 5-(aminomethyl)oxazolidin-3-one core of linezolid in enantiomerically pure form. The expedient cyclization of the -hydroxy amide derived from isoserine and 3-fluoro-4-morpholinoaniline to give the corresponding (aminomethyl)oxazolidine-2,4-dione, followed by its mild selective reduction at the C(4)-position, gave linezolid in almost quantitative overall yield.
Convenient Synthesis of the Antibiotic Linezolid via an Oxazolidine-2,4-dione Intermediate Derived from the Chiral Building Block Isoserine / Greco, A.; De Marco, R.; Tani, S.; Giacomini, D.; Galletti, P.; Tolomelli, A.; Juaristi, E.; Gentilucci, L.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2014:34(2014), pp. 7614-7620. [10.1002/ejoc.201402888]
Convenient Synthesis of the Antibiotic Linezolid via an Oxazolidine-2,4-dione Intermediate Derived from the Chiral Building Block Isoserine
De Marco, R.;Giacomini, D.;Galletti, P.;Tolomelli, A.;Gentilucci, L.
2014
Abstract
We describe a new synthesis of the 5-(aminomethyl)oxazolidin-3-one core of linezolid in enantiomerically pure form. The expedient cyclization of the -hydroxy amide derived from isoserine and 3-fluoro-4-morpholinoaniline to give the corresponding (aminomethyl)oxazolidine-2,4-dione, followed by its mild selective reduction at the C(4)-position, gave linezolid in almost quantitative overall yield.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
