GB673864A - Process for obtaining organic amino diols - Google Patents

Process for obtaining organic amino diols

Info

Publication number
GB673864A
GB673864A GB21748/49A GB2174849A GB673864A GB 673864 A GB673864 A GB 673864A GB 21748/49 A GB21748/49 A GB 21748/49A GB 2174849 A GB2174849 A GB 2174849A GB 673864 A GB673864 A GB 673864A
Authority
GB
United Kingdom
Prior art keywords
diol
reg
nitrophenyl
aminopropane
phenyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB21748/49A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Publication of GB673864A publication Critical patent/GB673864A/en
Expired legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Acid addition salts of (dl)-q -amino diols of the formula <FORM:0673864/IV (b)/1> where Y is hydrogen or an -NO2 group, R1 and R2 are the same or different and represent hydrogen, halogen, alkyl or alkoxy radicals, R3 is hydrogen or an alkyl radical, and X is halogen, or the bases corresponding to such salts, are obtained by treatment with thionyl chloride of (dl)-reg. amino diol derivatives of the formula <FORM:0673864/IV (b)/2> where R4 represents hydrogen or an acyl, e.g. aliphatic acyl, halogen substituted aliphatic acyl, benzoyl, substituted benzoyl or araliphatic radical, followed by hydrolysis of the intermediate compound so formed, and when the free base is desired, by neutralization of the salt. It is postulated that the intermediate compound has the formula <FORM:0673864/IV (b)/3> where R may be alkyl, halogen-substituted alkyl, phenyl, substituted phenyl or aralkyl. The alkyl, alkoxy, or aliphatic radicals contain not more than 4 carbon atoms. The reaction with thionyl chloride is carried out below 50 DEG C., preferably at 20 DEG to 35 DEG C., either in a solvent, e.g. benzene, toluene, xylene, chloroform or carbon tetrachloride, or preferably in presence of excess thionyl chloride. The hydrolysis is carried out by heating the reaction mixture at 60 DEG to 110 DEG C. with at least sufficient water to hydrolyse the intermediate product and excess thionyl halide. The products are recovered by evaporation to dryness, extraction or (free bases) by filtration. The process may be applied to a mixture of (dl)- reg. and (dl)-q forms of an amino diol derivative. It is postulated that the (dl)-q -diastereoisomer yields an intermediate of the formula <FORM:0673864/IV (b)/4> and is not changed in structural configuration during the process, although the acyl group or groups are removed, and the product is solely a (dl)-q amino diol acid addition salt. Examples describe the preparation of (1a), (dl)-q 1-p-nitrophenyl - 2 - aminopropane - 1,3 - diol and (1b) the corresponding hydrochloride, from (dl) - reg. - 1 - p - nitrophenyl - 2 - acetamido - propane-1,3-diol; (1c) and (1d), (dl)-q -1-p-nitrophenyl 2-aminopropane-1,3-diol and its hydrochloride from (c) (dl)-reg.-1-p-nitrophenyl-2-acetamido - 3 - acetoxypropane - 1 - ol, and (d) a mixture of (dl)-reg.- and (dl)-q -1-p-nitrophenyl - 2 - acetamidopropane - 1,3 - diol; (2) (dl) - q - 1 - phenyl - 2 - aminopropane - 1,3 - diol and its hydrochloride or hydrobromide are prepared from (a), (dl)-reg.-1-phenyl-2 acetamidopropane-1,3 diol, (b), (dl)-reg.-1-phenyl-2-acetamido - 3 - acetoxypropane - 1 - ol and thionyl bromide, (c), (dl)-reg.-1-phenyl-2-benzamidopropane-1,3-diol or (dl)-reg.-1-phenyl-2-chloracetimidopropane-1,3-diol, (d), a mixture of (dl)-reg.- and (dl)-q -1-phenyl-2-acetamidopropane-1,3-diol; (3) (dl)-q -1-o-methyl-p-nitrophenyl - 2 - aminopropane - 1,3 - diol and (dl)-q - 1 - o - methylphenyl - 2 - aminopropane - 1,3 - diol from (dl)-reg.-1-o-methyl-p-nitrophenyl-2-propionamidopropane-1,3-diol and (dl)-reg.-1-o - methylphenyl - 2 - propionamidopropane - 1,3-diol respectively; (4) (dl)-q -1-m-methoxyphenyl-2-aminopropane-1,3-diol and (dl)-q -1-p-nitro-m-methoxyphenyl - 2 - aminopropane - 1,3 - diol from (dl) - reg. - 1 - m - methoxyphenyl - 2 - phenylacetamidopropane - 1,3 - diol, and (dl) - reg. - 1 - p - nitro - m - methoxyphenyl - 2 - phenylacetamidopropane-1,3-diol respectively; (5) (dl) - q - 1 - (31,41 - dimethylphenyl) - 2 - aminopropane-1,3-diol, and (dl)-q -1-(21-nitro-41,51 - dimethylphenyl) - 2 - aminopropane - 1,3 - diol from (dl)-reg.-1-(31,41-dimethylphenyl)-2-acetamido - 3 - benzoxypropane - 1 - ol and (dl) - reg. - 1 - (21 - nitro - 41,51 - dimethylphenyl)-2 - acetamido - 3 - benzoxypropane - 1 - ol; (6) (dl) - q - 3 - (31 - chloro - 51 - nitrophenyl) - 2 - aminobutane-1,3-diol from (dl)-reg.-3-(31-chloro-51 - nitrophenyl) - 2 - acetamido - 1 - acetoxybutane - 3 - ol and (dl) - q - 3 - (31,51 - dichlorophenyl)-2-aminobutane-1,3-diol from (dl)-reg.-3 - (31,51 - dichlorophenyl) - 2 - acetamido - 1 - acetoxybutane - 3 - ol. Except where stated thionyl chloride is employed. The free base is liberated by making the reaction mixture alkaline with ammonia or sodium hydroxide. The products are suitable as intermediates of antibiotics; those of (1) and (2) may be used in preparing (l) - q - 1 - p - nitrophenyl - 2 - dichloracetamido-propane-1,3-diol. To prepare the starting materials, e.g. (dl)-reg.-acylamido acyloxy alcohol, the corresponding (dl)-reg. amino diol is acylated with an acyl anhydride at about 70 DEG C., or with an acyl halide, anhydride or ester in aqueous medium in the presence of basic substance. The alcohol compound so obtained gives the corresponding (dl)-reg. acylamido diol by hydrolysis with one equivalent of alkali in cold aqueous acetone. The (dl)-reg.-acylamido diol compound may be acylated at about 70 DEG C. with another acyl anhydride. Reference is made to Specifications 652,273 and 652,274. The Specification as open to inspection under Sect. 91 includes the conversion of the products of examples 2(a) and 2(d) to (dl)-q -1-phenyl-2-acetamido-1,3-diacetoxypropane by treatment with acetic anhydride and pyridine. The product of example 3(b) is converted to the sulphate. The free base obtained in example (4) is converted to salts such as the tartrate, camphor sulphonate or benzoate by reaction with an alcoholic solution of the corresponding acid. This subject-matter does not appear in the Specification as accepted.
GB21748/49A 1948-12-21 1949-08-22 Process for obtaining organic amino diols Expired GB673864A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US673864XA 1948-12-21 1948-12-21

Publications (1)

Publication Number Publication Date
GB673864A true GB673864A (en) 1952-06-11

Family

ID=22075662

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21748/49A Expired GB673864A (en) 1948-12-21 1949-08-22 Process for obtaining organic amino diols

Country Status (1)

Country Link
GB (1) GB673864A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3062839A (en) * 1959-06-11 1962-11-06 American Home Prod Dihydroxy-tertiary-butylamines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3062839A (en) * 1959-06-11 1962-11-06 American Home Prod Dihydroxy-tertiary-butylamines

Similar Documents

Publication Publication Date Title
US2513346A (en) Process for obtaining organic amino diols
GB673864A (en) Process for obtaining organic amino diols
GB630712A (en) Process of preparing intermediates useful in the preparation of penicill amine
US2904551A (en) Chemical compounds and processes of preparing the same
GB970969A (en) Dicarboxylic acids and their esters and a process for the preparation thereof
US2515240A (en) Nitrophenyl ketonic amino alcohols
GB998355A (en) Phenylalanine derivatives
US3024244A (en) Process for producing pyridoxine and intermediates
GB1080503A (en) Substituted acetic acids and a process for their preparation
US3555046A (en) Plicatin tetra-acetate and process for its production
US3414586A (en) Acetoamido derivatives
GB672164A (en) A process for the manufacture of pentaenes
GB2011415A (en) Process for the Production of Thiophosphoric Acid Esters
SU66870A1 (en) The method of obtaining 2-acyl-methylene-3-alkyl-benzthiazolines
GB716426A (en) Heterocyclic compounds
US2451310A (en) Alkyl esters of alpha-acylamino, alpha-cyano, beta-(3 indole)-propionic acid
GB652275A (en) Process for the manufacture of completely acylated organic amino diols
GB668235A (en) Process for the preparation of methionine derivatives
Glenn et al. Analgesics Derived from Tetrahydroacenaphthones1
GB688108A (en) Process for the manufacture of ª‡-acylamido-ª‰-acyloxypropiophenones
GB752332A (en) Improvements in or relating to n, mono substituted piperazines and process of preparing the same
GB1218005A (en) 3-NITRO-gamma-RESORCYLIC ACID ANILIDES AND PROCESS FOR PREPARING THEM
GB597446A (en) Improvements in or relating to organic compounds containing sulphur
GB722886A (en) Anaesthetics
GB711018A (en) Process for the production of 1-ú­-nitrophenyl-2-acylamidopropane-1,3-diols