GB796901A - Improvements in or relating to the preparation of 1-(ú­-nitro-phenyl)-2-acylamido-propane-1,3-diols - Google Patents

Improvements in or relating to the preparation of 1-(ú­-nitro-phenyl)-2-acylamido-propane-1,3-diols

Info

Publication number
GB796901A
GB796901A GB15459/56A GB1545956A GB796901A GB 796901 A GB796901 A GB 796901A GB 15459/56 A GB15459/56 A GB 15459/56A GB 1545956 A GB1545956 A GB 1545956A GB 796901 A GB796901 A GB 796901A
Authority
GB
United Kingdom
Prior art keywords
borohydride
nitrophenyl
diols
calcium
prepared
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
GB15459/56A
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of GB796901A publication Critical patent/GB796901A/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
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • 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

1 - (p - Nitrophenyl) - 2 - acylamidopropane-1 : 3-diols are prepared by reducing a b -phenylserine derivative of the general formula: <FORM:0796901/IV (b)/1> (wherein R1 is hydrogen or a hydrocarbon residue) with a metal borohydride, treating the resulting metal complex compound of b -(p-nitrophenyl)-serinol with a mild acylating agent and decomposing the resulting acylated metal complex compound (e.g. with aqueous mineral acid or aqueous alkali). Suitable borohydrides are those of lithium, sodium and especially the alkaline-earth metals, whilst acylation may be effected with acid halides or especially with esters of halogenated acids. In examples: (1) D - (-) - threo - b - (p - nitrophenyl) - serine methyl ester is stirred with an ethanolic solution of calcium borohydride (prepared in situ from sodium borohydride and calcium chloride), and the product is refluxed with methyl dichloroacetate and decomposed with dilute hydrochloric acid to form chloramphenicol; (2) the reducing agent in (1) is replaced by a calcium borohydride-tetrahydrofuran complex. Additional starting materials are listed, and reference is made to acetyl and benzoyl as acyl substituents.
GB15459/56A 1955-05-17 1956-05-17 Improvements in or relating to the preparation of 1-(ú­-nitro-phenyl)-2-acylamido-propane-1,3-diols Expired GB796901A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU796901X 1955-05-17

Publications (1)

Publication Number Publication Date
GB796901A true GB796901A (en) 1958-06-18

Family

ID=10980355

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15459/56A Expired GB796901A (en) 1955-05-17 1956-05-17 Improvements in or relating to the preparation of 1-(ú­-nitro-phenyl)-2-acylamido-propane-1,3-diols

Country Status (1)

Country Link
GB (1) GB796901A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102285896A (en) * 2011-09-19 2011-12-21 武汉武药制药有限公司 Method for synthesizing broad-spectrum antibiotic chloramphenicol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102285896A (en) * 2011-09-19 2011-12-21 武汉武药制药有限公司 Method for synthesizing broad-spectrum antibiotic chloramphenicol

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