BE515500A - - Google Patents

Info

Publication number

BE515500A

BE515500A BE515500DA BE515500A BE 515500 A BE515500 A BE 515500A BE 515500D A BE515500D A BE 515500DA BE 515500 A BE515500 A BE 515500A

Authority

BE

Belgium

Prior art keywords

solution

compound

solvent

benzene

compounds

Prior art date

Links

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• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 32
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical group [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 30
• 150000001875 compounds Chemical class 0.000 claims description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
• 239000000203 mixture Substances 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 13
• 229940083599 Sodium Iodide Drugs 0.000 claims description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
• 235000009518 sodium iodide Nutrition 0.000 claims description 10
• 239000002904 solvent Substances 0.000 claims description 10
• DNVPQKQSNYMLRS-APGDWVJJSA-N Ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-APGDWVJJSA-N 0.000 claims description 8
• DNVPQKQSNYMLRS-LNHMRCHQSA-N Ergosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3C([C@H]4[C@@](C)([C@H]([C@@H](/C=C/[C@H](C(C)C)C)C)CC4)CC3)=CC=2)CC1 DNVPQKQSNYMLRS-LNHMRCHQSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 6
• 239000007787 solid Substances 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 238000005695 dehalogenation reaction Methods 0.000 claims description 5
• 239000012442 inert solvent Substances 0.000 claims description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 3
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 238000005658 halogenation reaction Methods 0.000 claims 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
• SNHMUERNLJLMHN-UHFFFAOYSA-N Iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims 1
• 239000011701 zinc Substances 0.000 claims 1
• 229910052725 zinc Inorganic materials 0.000 claims 1
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
• 239000000243 solution Substances 0.000 description 23
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 238000002844 melting Methods 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• 229960000583 Acetic Acid Drugs 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
• 239000012362 glacial acetic acid Substances 0.000 description 7
• 230000005712 crystallization Effects 0.000 description 6
• 238000004364 calculation method Methods 0.000 description 5
• 238000002425 crystallisation Methods 0.000 description 5
• 239000007832 Na2SO4 Substances 0.000 description 4
• -1 acetoxy, propionyloxy Chemical group 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• 230000031700 light absorption Effects 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 229910052938 sodium sulfate Inorganic materials 0.000 description 4
• 235000011152 sodium sulphate Nutrition 0.000 description 4
• 239000011343 solid material Substances 0.000 description 4
• NYTOUQBROMCLBJ-UHFFFAOYSA-N Tetranitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)([N+]([O-])=O)[N+]([O-])=O NYTOUQBROMCLBJ-UHFFFAOYSA-N 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• 239000000543 intermediate Substances 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
• 239000011630 iodine Substances 0.000 description 3
• 239000003208 petroleum Substances 0.000 description 3
• 150000003431 steroids Chemical class 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• QOXPZVASXWSKKU-UEIWAABPSA-N 5α-ergosta-7,22-dien-3β-ol Chemical class C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC[C@H]21 QOXPZVASXWSKKU-UEIWAABPSA-N 0.000 description 2
• 210000001772 Blood Platelets Anatomy 0.000 description 2
• MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 2
• 239000007868 Raney catalyst Substances 0.000 description 2
• 229910000564 Raney nickel Inorganic materials 0.000 description 2
• NGEVNHYPVVOXPB-RZZBNZQCSA-N [(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1[C@@H](OC(C)=O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 NGEVNHYPVVOXPB-RZZBNZQCSA-N 0.000 description 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 230000000875 corresponding Effects 0.000 description 2
• 229960004544 cortisone Drugs 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 238000005984 hydrogenation reaction Methods 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 230000002194 synthesizing Effects 0.000 description 2
• PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• 229940057952 Methanol Drugs 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 238000007792 addition Methods 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 238000002845 discoloration Methods 0.000 description 1
• 150000002137 ergosterols Chemical class 0.000 description 1
• 235000019439 ethyl acetate Nutrition 0.000 description 1
• 238000005755 formation reaction Methods 0.000 description 1
• 150000004694 iodide salts Chemical class 0.000 description 1
• QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1