GB745900A - Acylaminodiols and method for preparing same - Google Patents
Acylaminodiols and method for preparing sameInfo
- Publication number
- GB745900A GB745900A GB15864/52A GB1586452A GB745900A GB 745900 A GB745900 A GB 745900A GB 15864/52 A GB15864/52 A GB 15864/52A GB 1586452 A GB1586452 A GB 1586452A GB 745900 A GB745900 A GB 745900A
- Authority
- GB
- United Kingdom
- Prior art keywords
- products
- propanediol
- racemic
- radical
- propanediols
- 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
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises threo-acylaminodiols of the general formula <FORM:0745900/IV(a)/1> (wherein R represents a hydrocarbon radical of 1-7 carbon atoms, X represents S or SO2, and Y represents an aliphatic carboxylic acylamino radical), and the manufacture thereof by: (a) acylating the corresponding free aminodiols (Y = NH2); (b) (when X is S) reducing compounds of the general formula <FORM:0745900/IV(a)/2> (preferably by means of an oxidizable aluminium alkoxide containing not more than 4 carbon atoms in each alkyl group); (c) (when X is SO2) oxidizing the corresponding compounds in which X is S (preferably with a percompound under acidic conditions). The starting materials for processes (a) and (b) are obtainable by the processes of Specifications 746,015 and 746,016 respectively. The radical represented by R in the general formula may be benzyl, a cycloalkyl or alkenyl radical, or especially an alkyl or aryl radical, whilst that represented by Y may be, for example, alkanoylamino, nitroalkanoylamino, alkylmercaptoalkanoylamino, or especially haloalkanoylamino, and preferably contains 1-4 carbon atoms. The products, which may exist in racemic or in optically active forms, are useful as antibiotic agents, especially in their dextro-rotatory forms, or as intermediates therefor. In examples (in which all acylaminodiols and aminodiols are threo forms) (1) a -acetylamino-b -hydroxy-4 -methylmercaptopropiophenone is reduced with aluminium isopropoxide in isopropanol to 2-acetylamino - 1 - (4 - methylmercaptophenyl)-1 : 3 - propanediol, which is oxidized with peracetic acid in acetone to the corresponding 4-methylsulphonyl compound; (2) 2-amino-1-(4-methylmercaptophenyl) - 1 : 3 - propanediol or either of its optically active isomers is dichloracetylated by heating with ethyl dichloracetate or by treatment with chloral cyanhydrin and triethylamine, and the products are oxidized as in (1) to the corresponding 2-dichloracetylamino-1 - (4 - methylsulphonylphenyl) - 1 : 3 - propanediols; the same products are obtained by dichloracetylation of the corresponding 2-amino-1 - (4 - methylsulphonylphenyl) - 1 : 3 - propanediols; chloral hydrate and an alkali metal cyanide may be used instead of chloral cyanhydrin, and calcium carbonate, sodium carbonate or pyridine instead of triethylamine. By analogous process are prepared: (3) 2-dibromacetylamino - 1 - (4 - methylmercapto - and 4 - methylsulphonyl - phenyl) - 1 : 3 - propanediols; (4) the racemic products of (2) by the process of (1); (5)-(7), (9) and (10) racemic 2-dichloracetylamin - 1 - (4 - ethyl -, - n propyl-, -n-butyl-, -benzyl- and -phenyl-mercapto-and - sulphonylphenyl) - 1 : 3 - propanediol; (8) racemic 2 - acetylamino - 1 - (4 - benzylmercapto - and - sulphonyl - phenyl) - 1 : 3-propanediol. Further products and the corresponding starting materials and intermediates are listed in which R and Y have the following additional meanings: p-tolyl, cyclohexyl, methallyl, iso - and tert. - butyl; iodoacetylamino, b - chloropropionylamino, trifluoracetylamino, a - methylpropionylamino and a : b -dichloropropionylamino. Still further radicals which may be represented by R and Y are: n-heptyl, isoamyl, allyl, cyclopentyl, o- and m-tolyl; mono- and di-bromacetylamino, difluoracetylamino, a - chloropropionylamino, trichloracetylamino, nitroacetylamino, methyl-and ethylmercaptoacetylamino, methylsulphonylacetylamino, butyrylamino, a : a - dichloropropionylamino, cyanoacetylamino, methoxyacetylamino, acrylylamino and a - hydroxypropionylamino.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US745900XA | 1951-10-01 | 1951-10-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB745900A true GB745900A (en) | 1956-03-07 |
Family
ID=22120396
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15864/52A Expired GB745900A (en) | 1951-10-01 | 1952-06-24 | Acylaminodiols and method for preparing same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB745900A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3543021A1 (en) * | 1985-12-05 | 1987-06-11 | Boehringer Mannheim Gmbh | IMPROVED METHOD FOR PRODUCING D-THREO-1- (P-METHYLSULFONYLPHENYL) -2-DICHLORACETAMIDO-PROPANDIOL-1,3- (THIAMPHENICOL) AND USE OF SUITABLE INTERMEDIATES |
EP0500177A1 (en) | 1991-02-21 | 1992-08-26 | ZAMBON GROUP S.p.A. | Process for the preparation of trans-(5R)-2,4,5-trisubstituted 2-oxazolines |
US5336664A (en) * | 1990-04-24 | 1994-08-09 | Zambon Group S.P.A. | Compositions having herbicidal activity containing N-alkyl-amides as active ingredient |
US7126005B2 (en) | 2003-10-06 | 2006-10-24 | Aurobindo Pharma Limited | Process for preparing florfenicol |
EP1785414A1 (en) * | 2005-11-09 | 2007-05-16 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the synthesis of intermediates of chloramphenicol or its analogues |
-
1952
- 1952-06-24 GB GB15864/52A patent/GB745900A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3543021A1 (en) * | 1985-12-05 | 1987-06-11 | Boehringer Mannheim Gmbh | IMPROVED METHOD FOR PRODUCING D-THREO-1- (P-METHYLSULFONYLPHENYL) -2-DICHLORACETAMIDO-PROPANDIOL-1,3- (THIAMPHENICOL) AND USE OF SUITABLE INTERMEDIATES |
US5336664A (en) * | 1990-04-24 | 1994-08-09 | Zambon Group S.P.A. | Compositions having herbicidal activity containing N-alkyl-amides as active ingredient |
US5556829A (en) * | 1990-04-24 | 1996-09-17 | Zambon Group S.P.A. | Compositions having herbicidal activity containing N-alkyl-amides as active ingredient |
EP0500177A1 (en) | 1991-02-21 | 1992-08-26 | ZAMBON GROUP S.p.A. | Process for the preparation of trans-(5R)-2,4,5-trisubstituted 2-oxazolines |
US7126005B2 (en) | 2003-10-06 | 2006-10-24 | Aurobindo Pharma Limited | Process for preparing florfenicol |
EP1785414A1 (en) * | 2005-11-09 | 2007-05-16 | KRKA, tovarna zdravil, d.d., Novo mesto | Process for the synthesis of intermediates of chloramphenicol or its analogues |
WO2007054147A1 (en) * | 2005-11-09 | 2007-05-18 | Krka | Process for the synthesis of intermediates of chloramphenicol or its analogues |
EA015270B1 (en) * | 2005-11-09 | 2011-06-30 | Крка | Process for the synthesis of intermediates of chloramphenicol or its analogues |
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