2-alkoxy-5(4H)-oxazolones and the enantiomerization of N-alkoxycarbonylamino acids

✍ Scribed by N. Leo Benoiton

• Book ID: 102650610
• Publisher: Wiley (John Wiley & Sons)
• Year: 1996
• Tongue: English
• Weight: 926 KB
• Volume: 40
• Category: Article
• ISSN: 0006-3525
• DOI: 10.1002/(sici)1097-0282(1996)40:2<245::aid-bip4>3.0.co;2-w

✦ Synopsis

2-Alkoxy-5 (4H) -oxazolones and the Enantiomerization of N-Alkoxycarbonylamino Acids *

N-Alkoxycurbonylamino a d s are chirully stuhk un&r normul conditions of coupling. In the presence oftert.amine (tertiary umine) , most uctivuted N-ulko.x.vcarhonylumino ucids generute 2-alkoxy-5 ( 4 H ) -oxazolone, which is not chiruI1.v stuhk in thc prescwce of thc base. Consequently, enantiomerization occurs in the prc.wncc~ oJ'tert.uminr if 'thc activaied residue is not immediately consiimed hy umino1.v.si.s. This puper rcvicrvs thc sit uutions in which 2-ulkoxy-S ( 4 H ) -oxuzolonrs ure gcwruted,from N-ulko.u.v~url~on~~lutnino ucid.v, the Linuntiomerizution thut occurs during and u1tc.r the incorporation of N-alkos.~~curhon.~~lutnin~~ uc.id.r into peptidc).s, the properties and methoh ofprcyxuution 0/'2-ulko~~j~-S (4H) -oxuzolones, und the pructicul use thut has heen mudo ,jrom our knowlodgc of the clwmistry of 2-ulko.uy-5 (4H) -o.wzoloncx 0 1996