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GB760933A - Process for the synthesis of chloramphenicol - Google Patents

Process for the synthesis of chloramphenicol

Info

Publication number
GB760933A
GB760933A GB25845/53A GB2584553A GB760933A GB 760933 A GB760933 A GB 760933A GB 25845/53 A GB25845/53 A GB 25845/53A GB 2584553 A GB2584553 A GB 2584553A GB 760933 A GB760933 A GB 760933A
Authority
GB
United Kingdom
Prior art keywords
threo
hydrochloride
nitrate
phenyl
salt
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
GB25845/53A
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 GB760933A publication Critical patent/GB760933A/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

Landscapes

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

Abstract

The synthesis of chloramphenicol described in Specification 729,617 is modified by conversion of the hydrochloride salt of the D-threo-1-phenyl - 1 : 3 - bis - acyloxy - 2 - aminopropane into the corresponding nitrate salt before nitration. The process is not limited to the particular reaction conditions claimed in the above Specification. The conversion of the hydrochloride into the nitrate is effected by treating a methanol solution of the former with an aqueous or methanol solution of a salt of a metal which forms an insoluble chloride, e.g. silver nitrate or lead nitrate. Examples show the synthesis of chloramphenicol from DL-threo-b -phenylserine (see Specification 687,214), passing through the following intermediates: (1) DL - threo - b - phenylserine cyclohexyl ester (via hydrochloride), L-threo-b -phenylserine cyclohexyl ester (via L-pyroglutamate salt), D - threo - 1 - phenyl - 2 - amino - 1 : 3-propanediol, D - threo - 1 - phenyl - 1 : 3-diacetoxy - 2 - aminopropane hydrochloride and nitrate, D - threo - 1 - p - nitrophenyl - 2-acetamido - 3 - acetoxy - 1 - propanol and D - threo - 1 - p - nitrophenyl - 2 - amino - 1 : 3-propanediol hydrochloride; (2) the first three as in (1) and then D-threo-1-phenyl-1 : 3-bis-(dichloracetoxy) - 2 - aminopropane hydrochloride and nitrate, and subsequent steps as in (1). Reference has been directed by the Comptroller to Specifications 707,571, 715,122, 715,123, 715,128, 729,550, 729,597 and 729,617.
GB25845/53A 1952-09-19 1953-09-18 Process for the synthesis of chloramphenicol Expired GB760933A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT760933X 1952-09-19

Publications (1)

Publication Number Publication Date
GB760933A true GB760933A (en) 1956-11-07

Family

ID=11315899

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25845/53A Expired GB760933A (en) 1952-09-19 1953-09-18 Process for the synthesis of chloramphenicol

Country Status (1)

Country Link
GB (1) GB760933A (en)

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