GB652275A - Process for the manufacture of completely acylated organic amino diols - Google Patents

Abstract

Completely acylated aminodiols, of the general formula <FORM:0652275/IV (b)/1> (wherein R3 represents hydrogen or an alkyl radical of not more than 4 carbon atoms, and R4 and R5 are the same or different and represent hydrogen, halogen, or alkyl or alkoxy radicals of not more than 4 carbon atoms) are manufactured by treating a compound of the general formula <FORM:0652275/IV (b)/2> (wherein R1 represents an amino or acylamido group and R2 hydrogen or an acyl radical) with an acyl anhydride or acyl halide in the presence of a basic substance (e.g. an inorganic base or preferably a tertiary organic base such as pyridine, quinoline, dimethylaniline, triethylamine or N-ethylpiperidine) under substantially anhydrous conditions, advantageously by heating at about 60-130 DEG C. The starting materials and the products exist as structural (regular and pseudo) and optical isomers. Examples describe the acetylation, by means of acetic anhydride in the presence of pyridine, of: (1) dl-reg.-1-phenyl-2-dichloracetamidopropane - 1 : 3 - diol; (2) dl - q - 1 - phenyl - 2 - acetamido - 3 - acetoxypropane - 1 - ol; (3) dl-reg.-1-phenyl - 2 - aminopropane - 1 : 3 - diol; (4) dl-q -1-o-methylphenyl-2-acetamido-propane-1 : 3-diol or p -3-acetoxypropane-1-ol; (5) dl - q - 1 - m - methoxyphenyl - 2 - acetamido - 3 - acetoxypropane-1-ol; (6) dl-reg.-1-(31 : 41-dimethylphenyl)-2-aminopropane - 1 : 3 - diol; (7) dl-q -1-acetoxy-2-acetamido - 3 - phenylbutane - 3 - ol; (8) 1 - o - chlorophenyl-2-aminopropane-1 : 3-diol. Specifications 652,262, 652,273, 652,274, 652,276, 652,277, 652,278, 652,279 and 652,280 are referred to. The Specification as open to inspection under Sect. 91 comprises also the subject-matter of the aforementioned Specifications, and alternative processes for preparing the products of certain of them. This subject-matter does not appear in the Specification as accepted.