GB731397A - Phenylaminopropanediols and their derivatives - Google Patents
Phenylaminopropanediols and their derivativesInfo
- Publication number
- GB731397A GB731397A GB7039/53A GB703953A GB731397A GB 731397 A GB731397 A GB 731397A GB 7039/53 A GB7039/53 A GB 7039/53A GB 703953 A GB703953 A GB 703953A GB 731397 A GB731397 A GB 731397A
- Authority
- GB
- United Kingdom
- Prior art keywords
- threo
- hydrolysed
- acid chloride
- chloramphenicol
- nitrophenyl
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aminopropanediols of the formula <FORM:0731397/IV (b)/1> where R1 is hydrogen or nitro and R2 is hydrogen or an aliphatic acyl group of 1-8 carbon atoms (optionally substituted by halogen) are prepared by reducing with sodium borohydride an acid chloride of the formula <FORM:0731397/IV (b)/2> where R3 and R4 are acyl groups as defined for R2, and hydrolysing the product to remove the group R4 and if desired the group R3 also. The reduction step is preferably carried out in an inert organic solvent such as dioxane. Partial hydrolysis may be effected with decinormal caustic soda and acetone at room temperature. For complete hydrolysis 5 per cent hydrochloric acid can be used. The starting materials can be of the erythro or threo form and may be optically active or racemic. They are obtained from the corresponding acids by treatment with thionyl chloride or phosphorus pentachloride. The products (R1=NO2, R2=H) can be converted into chloramphenicol as in Specification 718,580. In the examples: (1) the acid chloride of (-)-threo - N - dichloracetyl - O - acetyl - p - nitrophenylserine is reduced to O-acetyl-chloramphenicol and the latter hydrolysed to chloramphenicol; (2) the acid chloride of racemic erythro - O : N - diacetyl - p - nitrophenylserine is reduced to 1-(p-nitrophenyl)-1-acetoxy - 2 - acetamido - 3 - propanol and the product hydrolysed to dl-erythro-1-(p-nitrophenyl) - 2 - amino - 1 : 3 - propanediol; (3) the acid chloride of (-)-threo-O : N-diacetylphenylserine is reduced to (-)-threo-1-phenyl-1-acetoxy - 2 - acetamido - 3 - propanol which can be either hydrolysed to (-)-threo-1-phenyl-2 - amino - 1 : 3 - propanediol or acylated, nitrated and hydrolysed to give (-)-threo-1-(p - nitrophenyl) - 2 - amino - 1 : 3 - propanediol.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT731397X | 1952-03-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB731397A true GB731397A (en) | 1955-06-08 |
Family
ID=11315236
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7039/53A Expired GB731397A (en) | 1952-03-17 | 1953-03-13 | Phenylaminopropanediols and their derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB731397A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3036094A (en) * | 1955-08-08 | 1962-05-22 | Bayer Ag | 1-phenyl-2-azidoacylamino-1, 3-propane diols |
-
1953
- 1953-03-13 GB GB7039/53A patent/GB731397A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3036094A (en) * | 1955-08-08 | 1962-05-22 | Bayer Ag | 1-phenyl-2-azidoacylamino-1, 3-propane diols |
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