GB705370A - Method of preparing racemic and levo-rotatory chloramphenicol from 1-acetoxy-3-oxo-3-phenyl-propane - Google Patents

Method of preparing racemic and levo-rotatory chloramphenicol from 1-acetoxy-3-oxo-3-phenyl-propane

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Publication number
GB705370A
GB705370A GB12763/50A GB1276350A GB705370A GB 705370 A GB705370 A GB 705370A GB 12763/50 A GB12763/50 A GB 12763/50A GB 1276350 A GB1276350 A GB 1276350A GB 705370 A GB705370 A GB 705370A
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GB
United Kingdom
Prior art keywords
acetoxy
phenyl
oxo
threo
propane
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
GB12763/50A
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.)
Gruppo Lepetit SpA
Original Assignee
Lepetit 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 Lepetit SpA filed Critical Lepetit SpA
Publication of GB705370A publication Critical patent/GB705370A/en
Expired legal-status Critical Current

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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

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

Abstract

A method of preparing (dl)-threo-1-p-nitrophenyl - 2 - dichloracetamino - 1, 3 - propandiol or (l)-threo-1-p-nitrophenyl-2-dichloracetamino-1, 3-propandiol (chloramphenicol) comprises reacting 1 - acetoxy - 3 - oxo - 3 - phenyl - propane with a nitrite in the presence of an acid to form 1-acetoxy-2-isonitroso-3-oxy-3-phenyl-propane, reacting such product under such mild conditions that the 3-oxo group is unchanged with a reducing agent in the presence of an acetylating agent to produce 1-acetoxy-2-acetamino-3-oxo-3-phenyl propane, reducing the latter with a more vigorous reducing agent to obtain a mixture of the diastereoisomeric threo and erythro form of 1-acetoxy-2-acetylamino-3-phenyl - 3 - propanol, treating the mixture obtained with concentrated sulphuric acid as in Specification 671,531, subjecting the oxazoline derivative so formed in the sulphuric acid solution to the action of fuming nitric acid, extracting the nitrated product with a water-immiscible organic solvent, hydrolyzing the nitrated product with dilute hydrochloric acid to effect opening of the oxazoline ring with the formation of (dl)-1-p-nitrophenyl-2-amino-1, 3-propandiol of only threo form and then either subjecting the product to N-dichloracetylation to form the (dl)-threo-1-p-nitrophenyl-2-dichloracetamino-1, 3-propandiol, or to resolution into the d- and l-rotatory isomers as in Specification 674,015 and N-dichloracetylating the separated 1-isomer to form the (l)-threo-1-p-nitrophenyl-2-dichloracetamino-1, 3-propandiol (chloramphenicol). In the first stage sodium nitrite in acetic acid or an alkyl nitrite in ether in the presence of hydrochloric acid may be employed. The intermediate products need not be isolated. In an example illustrating the process the 1-acetoxy-2-isonitroso-3-oxo-3-phenyl-propane is converted by reaction with zinc, acetic acid and acetic anhydride to the 1-acetoxy-2-acetamino-3-oxo-3-phenylpropane. The latter is hydrogenated using a palladium-carbon catalyst to give the 1-acetoxy-2-acetamino-3-phenyl-3-propanol, the remaining stages being carried out as above. Specification 652,273 also is referred to.
GB12763/50A 1949-12-22 1950-05-22 Method of preparing racemic and levo-rotatory chloramphenicol from 1-acetoxy-3-oxo-3-phenyl-propane Expired GB705370A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT705370X 1949-12-22

Publications (1)

Publication Number Publication Date
GB705370A true GB705370A (en) 1954-03-10

Family

ID=11314034

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12763/50A Expired GB705370A (en) 1949-12-22 1950-05-22 Method of preparing racemic and levo-rotatory chloramphenicol from 1-acetoxy-3-oxo-3-phenyl-propane

Country Status (1)

Country Link
GB (1) GB705370A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113004165A (en) * 2019-12-19 2021-06-22 武汉武药制药有限公司 Preparation method of chloramphenicol impurity compound I

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113004165A (en) * 2019-12-19 2021-06-22 武汉武药制药有限公司 Preparation method of chloramphenicol impurity compound I

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