Synthesis and Resolution of 3-Amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones

Article abstract of DOI:10.1021/jo00391a010

Two efficient synthetic routes to the 3-amino-1,4-benzodiazepin-2-ones 2 and 3 were developed.The first sequence was carried out in 55-60percent overall yield and involves a novel mercuric ion assisted ammonia displacement of the (alkylthio)glycinamide 14 to produce the key intermediate α-aminoglycinamide 15.The second approach features a practical two-step amination of the parent 1,4-benzodiazepine ring system 24 to afford the title compound 3 in 49percent overall yield from 2-aminobenzophenone.The 3-amino-1,4-benzodiazepine 3 was resolved via the separation of the corresponding diastereomeric phenylalanyl amides.The desired (-)-3 enantiomer was then liberated by use of the Edman degradation.