クロルアンフェニコール合成研究 (第9報)

1-p-Nitrophenyl-2-amino-1, 3-propanediolの有機酸塩を別種の有機酸でアシル化する方法

抄録

By the extension of the reaction reported in the previous paper, organic acid was reacted with 1-p-nitrophenyl-2-amino-1, 3-propanediol (aminodiol) (I). By the heating of aminodiol benzoate (II) with excess of acetic acid in butanol, N-acetylaminodiol (III) was obtained in a 69% yield. The use of equimolar amount of acetic acid, in this case, results in the decrease of the yield to 10% with recovery of unreacted (II). Application of equimolar amount of acetic acid and excess of benzoic acid to (I) gives (II) alone and no formation of (III) was detected. By the application of dichloroacetic acid to d- and l-aminodiol tartrate in butanol, the natural-form chloramphenicol (d-V) and its antipode (l-V) were obtained with 40% yield. d-Compound, [α]_D²²=+19.07° (c=1.52% EtOH); antibacterial power 1000u/mg.