Patent ID: 6573387
Filing Date: 2003-06-03
Classification: C07C,C07D,C40B

Abstract:
A method for converting an &agr;,&bgr;-saturated amide substrate to a blocked or unblocked &agr;,&bgr;-substituted amino amide product, the blocked &agr;,&bgr;-substituted amino amide product having a blocked amino group, the method comprising the following steps:Step 1) Oxidizing the &agr;,&bgr;-unsaturated amide substrate with a nitrogen source for making a racemic mixture of an &agr;,&bgr;-hydroxy-amino amide intermediate having a blocked amino group; then Step 2) Cyclodehydrating the &agr;,&bgr;-hydroxy-amino amide intermediate described in step 1 for producing an &agr;,&bgr;-N-blocked-aziridine amide intermediate having an aziridine ring; then Step 3) Opening the aziridine ring of the &agr;,&bgr;-N-blocked-aziridine amide intermediate described in step 2 with a nucleophile in a regioselective manner for making the blocked &agr;,&bgr;-substituted amino amide product; and then p1 Step 4) Optionally deblocking the amino group of the blocked &agr;,&bgr;-substituted amino amide product to produce the unblocked &agr;,&bgr;-substituted amino amide product.