GB736407A - Manufacture of oxo-acylamines of the cyclopentanopolyhydrophenanthrene series - Google Patents

Info

Publication number

GB736407A

GB736407A GB14396/52A GB1439652A GB736407A GB 736407 A GB736407 A GB 736407A GB 14396/52 A GB14396/52 A GB 14396/52A GB 1439652 A GB1439652 A GB 1439652A GB 736407 A GB736407 A GB 736407A

Authority

GB

United Kingdom

Prior art keywords

hydroxy

acetylamino

oxo

androstene

compound

Prior art date

1951-06-06

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

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• 238000004519 manufacturing process Methods 0.000 title 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 8
• SBNLPRGISFUZQE-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 SBNLPRGISFUZQE-VMXHOPILSA-N 0.000 abstract 4
• IATKKATWPOVYCC-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IATKKATWPOVYCC-VMXHOPILSA-N 0.000 abstract 4
• WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 4
• 229960000583 acetic acid Drugs 0.000 abstract 4
• 239000012362 glacial acetic acid Substances 0.000 abstract 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
• 239000004411 aluminium Substances 0.000 abstract 2
• 229910052782 aluminium Inorganic materials 0.000 abstract 2
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 2
• 150000001875 compounds Chemical class 0.000 abstract 2
• -1 isobutyryl Chemical group 0.000 abstract 2
• 238000000034 method Methods 0.000 abstract 2
• 239000007800 oxidant agent Substances 0.000 abstract 2
• 230000003647 oxidation Effects 0.000 abstract 2
• 238000007254 oxidation reaction Methods 0.000 abstract 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
• LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 abstract 2
• JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 abstract 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
• GDSSWKSLDBUUPM-XTMXWQDMSA-N N-[(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]acetamide Chemical compound O=C1C[C@@H]2CC[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)NC(C)=O)C)[C@]2(CC1)C GDSSWKSLDBUUPM-XTMXWQDMSA-N 0.000 abstract 1
• WZBCNGZGBLYICC-CSPYRVFGSA-N N-[(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]propanamide Chemical compound O=C1C[C@@H]2CC[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)NC(CC)=O)C)[C@]2(CC1)C WZBCNGZGBLYICC-CSPYRVFGSA-N 0.000 abstract 1
• SEPTUUZCQJZKSS-GUTNPPIESA-N N-[(5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]acetamide Chemical compound OC1C[C@@H]2CC[C@@H]3[C@H](CC[C@@]4(C(CC[C@H]43)NC(C)=O)C)[C@]2(CC1)C SEPTUUZCQJZKSS-GUTNPPIESA-N 0.000 abstract 1
• HMNQNULAYXDEEQ-UHFFFAOYSA-N acetic acid;hydroxylamine Chemical compound ON.CC(O)=O HMNQNULAYXDEEQ-UHFFFAOYSA-N 0.000 abstract 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
• 230000000397 acetylating effect Effects 0.000 abstract 1
• 239000002253 acid Substances 0.000 abstract 1
• 239000003513 alkali Substances 0.000 abstract 1
• 238000009835 boiling Methods 0.000 abstract 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
• 229910052794 bromium Inorganic materials 0.000 abstract 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
• 125000004432 carbon atom Chemical group C* 0.000 abstract 1
• KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 abstract 1
• 238000007256 debromination reaction Methods 0.000 abstract 1
• AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 abstract 1
• 229910052736 halogen Inorganic materials 0.000 abstract 1
• 150000002367 halogens Chemical class 0.000 abstract 1
• 230000003301 hydrolyzing effect Effects 0.000 abstract 1
• 239000012442 inert solvent Substances 0.000 abstract 1
• 150000002576 ketones Chemical class 0.000 abstract 1
• 229910052751 metal Inorganic materials 0.000 abstract 1
• 239000002184 metal Substances 0.000 abstract 1
• 239000000203 mixture Substances 0.000 abstract 1
• 230000001590 oxidative effect Effects 0.000 abstract 1
• 150000002923 oximes Chemical class 0.000 abstract 1
• IXAXVYMFIJYCSG-UHFFFAOYSA-N pentan-1-one Chemical compound CCCC[C]=O IXAXVYMFIJYCSG-UHFFFAOYSA-N 0.000 abstract 1
• 238000002360 preparation method Methods 0.000 abstract 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
• 239000000376 reactant Substances 0.000 abstract 1
• 229920006395 saturated elastomer Polymers 0.000 abstract 1
• 230000009466 transformation Effects 0.000 abstract 1