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-propaneInfo
- 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
- Authority
- 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
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
Landscapes
- 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.
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)
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 |
-
1950
- 1950-05-22 GB GB12763/50A patent/GB705370A/en not_active Expired
Cited By (1)
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 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB705370A (en) | Method of preparing racemic and levo-rotatory chloramphenicol from 1-acetoxy-3-oxo-3-phenyl-propane | |
GB761093A (en) | Production of s-acetyl glutathione | |
GB695170A (en) | Method of purifying organic compounds | |
SU138030A1 (en) | The method of producing polycarbonates | |
US2468436A (en) | Method of producing carboxylic aliphatic nitriles | |
US2212363A (en) | Process of preparing compounds having the character of the male sexual hormones | |
US2453942A (en) | Nitration of alcohols | |
US3153090A (en) | Process for the production of oximes | |
DE953170C (en) | Process for the degradation of quaternary aromatic ammonium compounds to tertiary aromatic amines | |
GB722594A (en) | Improvements in the manufacture of cellulose esters | |
FR848740A (en) | Process for preparing nitric esters of monacylated glycerins | |
SU143388A1 (en) | Method for producing alpha-hydroxyisobutyric acid | |
GB912036A (en) | 11-methylene-5ª--steroids | |
US1168164A (en) | Derivatives of cellulose containing the residue of an organic acid and nitrogen and process of making same. | |
GB694490A (en) | Improved process for preparing 4,6,2:4,6-hexanitrodiphenylamine | |
GB1457499A (en) | Process for the preparation of anthraquinone | |
GB455264A (en) | Process for the manufacture of esters of polycyclic alcohols | |
GB621531A (en) | Manufacture of chlorinated aliphatic acids | |
GB748600A (en) | Process for the production of the methobromide of a basic ester | |
GB662229A (en) | Improvements relating to the oxidation of aromatic side-chain compounds | |
GB877884A (en) | Process for producing para-nitrodiarylamines | |
GB799272A (en) | Production of intermediates for the synthesis of reserpine and analogous compounds | |
GB695769A (en) | Process for the manufacture of d-threo-1-p-nitrophenyl-2-dichloroacetylamino-1,3-propandiol | |
ES264322A1 (en) | New steroid compounds and their formation | |
FR2445825A1 (en) | PROCESS FOR THE PREPARATION OF 3-PHENOXYBENZALDEHYDE |