GB729617A - Process for the synthesis of chloramphenicol - Google Patents

Process for the synthesis of chloramphenicol

Info

Publication number
GB729617A
GB729617A GB10808/53A GB1080853A GB729617A GB 729617 A GB729617 A GB 729617A GB 10808/53 A GB10808/53 A GB 10808/53A GB 1080853 A GB1080853 A GB 1080853A GB 729617 A GB729617 A GB 729617A
Authority
GB
United Kingdom
Prior art keywords
give
threo
nitrophenyl
propanediol
hydrochloride
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
GB10808/53A
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.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
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 Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Publication of GB729617A publication Critical patent/GB729617A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Chloramphenicol is prepared by esterifying racemic b -phenylserine to racemic threo-b -phenylserine cyclohexyl ester; resolving the ester by combination with an optically active acid and fractional crystallization; reducing the dextrorotatory form (L-three-b -phenyl serine cyclohexyl ester) in an organic solvent by a method known to be capable of reducing the carbalkoxy group to carbinol to give D-threo-1-phenyl - 2 - amino - 1 : 3 - propanediol; 0 : 0-bisdichloroacetylation of this in an anhydrous solvent free from alcoholic and basic groups preferably dichloroacetic acid acidified with a solution of hydrochloric acid in the same type of solvent, dichloroacetylating with dichloroacetyl chloride at a temperature below 35 DEG C. to produce the desired 0 : 0-bisdichloroacetyl hydrochloride; nitrating at below 0 DEG C. to give the p-nitrophenyl derivative, and alkalizing to effect migration of one dichloroacetyl group from the O to the N position while saponifying the other to give D-threo-1-p-nitrophenyl-2-dichloroacetamido - 1 : 3 - propanediol (chloramphenicol). An alternative procedure comprises esterification of b -phenylserine to the cyclohexyl ester, resolution into optical isomers and reduction as in the above method to give D-threo - 1 - phenyl - 2 - amino - 1 : 3 - propanediol; 0 : 0-diacetylation of this with acetyl chloride at a temperatre below 35 DEG C. in a solvent free from alcoholic or basic groups which is acidified with a solution of hydrochloric acid in a solvent of the same type to give the 0 : 0-diacetyl hydrochloride; nitration of this at a temperature below 0 DEG C. to obtain the corresponding nitrophenyl compound; alkalizing to a pH between 7 and 8 to cause migration of an acetyl group to give D-threo-1-p-nitrophenyl-2-acetamido - 3 - acetoxy propan -1-ol; saponifying to give D-threo-1-p-nitrophenyl-2-amino-1 : 3-propanediol hydrochloride; treating this with dichloroacetyl chloride in dichloroacetic acid saturated with hydrochloric acid to give the 0 : 0-biodichloroacetyl hydrochloride and alkalizing to a pH higher than 7 to cause migration of a dichloroacetyl group from O to N with contemporaneous saponification to give the desired D - threo - 1 - p - nitrophenyl - 2 - dichloroacetamido p - 1 : 3 - propane diol. Examples are given. Specifications 687,214, 707,571, 715,122, 715,123 and 715,128 are referred to.
GB10808/53A 1951-11-05 1951-12-04 Process for the synthesis of chloramphenicol Expired GB729617A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT729617X 1951-11-05

Publications (1)

Publication Number Publication Date
GB729617A true GB729617A (en) 1955-05-11

Family

ID=11315199

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10808/53A Expired GB729617A (en) 1951-11-05 1951-12-04 Process for the synthesis of chloramphenicol

Country Status (1)

Country Link
GB (1) GB729617A (en)

Similar Documents

Publication Publication Date Title
Cartwright The structure of serratamic acid
GB729617A (en) Process for the synthesis of chloramphenicol
FR1167788A (en) Process for the production of organic carboxylic acid esters
US2681364A (en) Process for the production of 1-p-nitrophenyl-2-acylamidopropane-1,3-diols
FR1175585A (en) Process for manufacturing organic compounds, in particular acetic acid
ES389253A1 (en) 2-substituted phenyl propionic acids
US3852333A (en) New anthranilic acid{60 -monoglycerides
DE3369975D1 (en) Threo-adrenalinecarboxylic acid, processes for the production thereof, and pharmaceutical compositions thereof
FR1084438A (en) Improvements in the preparation of propyl nitrate
DE828551C (en) Process for the resolution of racemic threo-1- (4'-nitro-phenyl) -2-dichloroacetylamino-propanediol- (1,3) into its optical isomers
ES400792A1 (en) Procedure for the preparation of new acids 4- (4-bifenilil) -butiricos and their steres. (Machine-translation by Google Translate, not legally binding)
US2707194A (en) Mandelic acid esters of nu-octanol-1 and nu-nonanol-1
GB868483A (en) New intermediates in the synthesis of reserpine and their preparation
GB695769A (en) Process for the manufacture of d-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propandiol
YU46803B (en) PROCEDURE FOR OBTAINING NEW HYDROXIAMINO-EBURNANE DERIVATIVES
GB396575A (en) Process for the preparation of a new type of fibrous cellulose ester
GB731397A (en) Phenylaminopropanediols and their derivatives
FR1282638A (en) New process for the saponification of organic carboxylic acid esters of an estrene derivative
GB715123A (en) Process for preparing threo-1-phenyl-1, 3-diacyloxy-2-amino-propane hydrochlorides
ES414791A1 (en) Indol-7-ylacetic acids and esters thereof
GB755846A (en) Optical isomers of n-n-diethyl-n(2-tetrahydro-1,2,3,4-naphthyl) glycineamide, salts thereof, and process for preparing the same
GB615602A (en) Improvements in and relating to a process for the manufacture of mixed esters of cellulose and of films thereof
GB1461787A (en) Preparation of substituted decenoic acids
GB795131A (en) Improvements in or relating to the preparation of primary alcohols
FR806584A (en) Process for the production of organic acid anhydrides