Tetrahedron letters

An alternate enantiospecific synthesis of methyl (S)-7-tert-butoxycarbonyl-2, 3, 4, 5-tetrahydro-4-methyl-3-oxo-1H-1, 4-benzodiazepine-2-acetate

TW Ku, FE Ali, WE Bondinell, KF Erhard, WF Huffman…

Index: Ku, Thomas W.; Ali, Fadia E.; Bondinell, William E.; Erhard, Karl F.; Huffmann, William F.; et al. Tetrahedron Letters, 1997 , vol. 38, # 18 p. 3131 - 3134

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Citation Number: 21

Abstract

An alternate enantiospecific synthesis of methyl (S)-7-tert-butoxycarbonyl-2, 3, 4, 5- tetrahydro-4-methyl-3-oxo-1H-1, 4-benzodiazepine-2-acetate (5) is reported. The key step, which involves an intermolecular displacement of the activated aryl fluoride (9) by L-aspartic acid β-methyl ester, proceeds without racemization.