GB711018A - Process for the production of 1-ú­-nitrophenyl-2-acylamidopropane-1,3-diols - Google Patents

Abstract

1 - Para - nitrophenyl - 2 - acylamidopropane - 1,3-diols of the formula <FORM:0711018/IV (b)/1> wherein "acyl" represents a carboxylic acid acyl radical such as a lower aliphatic acyl, halogen substituted lower aliphatic acyl, hydroxyl substituted lower aliphatic acyl (lower aliphatic implying not more than four carbon atoms), benzoyl substituted with non-reducible groups such as halogen, alkoxy, alkyl and hydroxyl groups, and araliphatic acyl radicals, are prepared by reacting, preferably below 50 DEG C., an a -acylamido-b -hydroxy-para-nitropropiophenone or a derivative thereof of the formula <FORM:0711018/IV (b)/2> wherein R is hydrogen or a carboxylic acid acyl radical, with sodium or potassium borohydrides in a non-acidic hydroxylic solvent (e.g. water or methanol, ethanol, isopropanol and aqueous solutions thereof) and hydrolysing the boron complex so formed, preferably with dilute acids. Specified starting materials are a -dichloroacetamido - b - hydroxy - para - nitropropiophenone, a - acetamido - b - hydroxy - paranitropropiophenone, b -acetoxy derivatives thereof, a -benzamido - b - hydroxy - para - nitropropiophenone (including cases where the benzamido group is substituted with para-methyl, meta-methoxy and para-bromo groups), a -dichloroacetamido-b - dichloroacetoxy - para - nitropropiophenone, a - methoxyacetamido - b - hydroxy - para - nitropropiophenone and a - phenylacetamido - b - hydroxy - para - nitropropiophenone. The use of b -acyloxy ketonic starting materials favours the formation of the regular (erythro) diastereoisomer while use of b -hydroxy ketonic compounds results in practically equal mixtures of the two diastereoisomeric forms of the acylamido-diol product. The examples describe the preparation of (dl)-reg. and (dl)-#Y-1-paranitrophenyl - 2 - acetamidopropane - 1,3 - diols, (dl) - reg. and (dl) - #Y - 1 - para - nitrophenyl - 2 - dichloroacetamidopropane - 1,3 - diols, (dl)-reg.- and (dl) - #Y - 1 - para - nitrophenyl - 2 - benzamidopropane - 1,3 - diols (including cases where the benzamido group is substituted with para-methyl, meta-methoxy and para-bromo groups), (dl)-reg.- and (dl)-#Y-para-nitrophenyl-2-methoxyacetamidopropane - 1,3 - diols, and (dl) - reg.- and (dl) - #Y - para - nitrophenyl - 2 - phenylacetamidopropane-1,3-diols.