GB808279A - Manufacture of hydrophenanthryl-carboxylic acids and functional derivatives thereof - Google Patents
Manufacture of hydrophenanthryl-carboxylic acids and functional derivatives thereofInfo
- Publication number
- GB808279A GB808279A GB13787/55A GB1378755A GB808279A GB 808279 A GB808279 A GB 808279A GB 13787/55 A GB13787/55 A GB 13787/55A GB 1378755 A GB1378755 A GB 1378755A GB 808279 A GB808279 A GB 808279A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetoxy
- free
- diketo
- group
- testane
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- HMNQNULAYXDEEQ-UHFFFAOYSA-N acetic acid;hydroxylamine Chemical compound ON.CC(O)=O HMNQNULAYXDEEQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001443 androstenes Chemical class 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- -1 steroid lactam Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Abstract
The invention comprises hydrophenanthrylcarboxylic acids and their esters having the general formula <FORM:0808279/IV (b)/1> in which n represents the whole number 2 or 3, X represents a free or esterified carboxyl group, R represents a free, or an enolized or ketalized oxo group or the group <FORM:0808279/IV (b)/2> , in which R1 represents a free or esterified hydroxyl group, and their derivatives having a double bond extending from the 14-carbon atom and a process for the preparation of such compounds wherein a steroid lactam of the general formula <FORM:0808279/IV (b)/3> in which n and R have the meanings given above, or their derivatives having a double bond extending from the 5-carbon atom, are treated with a solution of an alkali metal hydroxide or an alkali metal alcoholate and, if desired, free hydrophenanthryl carboxylic acids obtained are converted into their esters. The treatment with alkali metal hydroxide may be carried out at elevated temperature and pressure in the presence of an organic solvent, e.g. an alcohol. The substituent in the 3-position in the starting material may be acetoxy or a keto group ketolized with ethylene glycol. In an example, D 2 - 2,13 - dimethyl - 4 - keto - 7a - hydroxy - dodecahydro - phenanthryl - (1) - propionic acid is obtained by heating 3a -acetoxy-11,17-diketo - 17a - azo - D - homo - testane with alcoholic caustic potash under pressure. The corresponding -(1)-propionic methyl ester is obtained by treating the free acid with diazomethane. The products of the process may be used as starting materials in the process of Specification 805,604. Starting materials for use in the present process are prepared by converting the corresponding substituted 11, 17-dioxo-D-homotestanes or androstenes into the 17- or 17a -monoximes and subjecting the latter to a Beckmann re-arrangement. 3a - Acetoxy - 11,17 - diketo - 17a - aza - D-homo-testan is obtained by reacting 3a -acetoxy - 11,17 - diketo - testane with hydroxylamine acetate in ethanol, separating the 3a -acetoxy - 11,17 - diketo - testane 17 - monoxime, heating the latter with p-acetylaminobenzene sulphonic acid chloride and pyridine, heating the reaction mixture with water and extracting with a mixture of ether and chloroform.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH808279X | 1954-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB808279A true GB808279A (en) | 1959-02-04 |
Family
ID=4538263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13787/55A Expired GB808279A (en) | 1954-05-26 | 1955-05-12 | Manufacture of hydrophenanthryl-carboxylic acids and functional derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB808279A (en) |
-
1955
- 1955-05-12 GB GB13787/55A patent/GB808279A/en not_active Expired
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