BE512966A - - Google Patents

Info

Publication number

BE512966A

BE512966A BE512966DA BE512966A BE 512966 A BE512966 A BE 512966A BE 512966D A BE512966D A BE 512966DA BE 512966 A BE512966 A BE 512966A

Authority

BE

Belgium

Prior art keywords

compounds

denotes

general formula

acid

following general

Prior art date

Links

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• 150000001875 compounds Chemical class 0.000 claims description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
• KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
• 238000000034 method Methods 0.000 claims description 6
• 239000007788 liquid Substances 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 4
• 125000001931 aliphatic group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 230000003647 oxidation Effects 0.000 claims description 3
• 238000007254 oxidation reaction Methods 0.000 claims description 3
• 239000011701 zinc Substances 0.000 claims description 3
• 229910052725 zinc Inorganic materials 0.000 claims description 3
• 125000004423 acyloxy group Chemical group 0.000 claims description 2
• 150000002148 esters Chemical class 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 239000003960 organic solvent Substances 0.000 claims description 2
• 239000000126 substance Substances 0.000 claims description 2
• OWAQXCQNWNJICI-UHFFFAOYSA-N benzene;chloroform Chemical compound ClC(Cl)Cl.C1=CC=CC=C1 OWAQXCQNWNJICI-UHFFFAOYSA-N 0.000 claims 1
• 239000002904 solvent Substances 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 229960000583 Acetic Acid Drugs 0.000 description 5
• 238000002844 melting Methods 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 4
• 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 3
• 238000004458 analytical method Methods 0.000 description 3
• 229960004544 cortisone Drugs 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• 239000003208 petroleum Substances 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• 150000003431 steroids Chemical class 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000005712 crystallization Effects 0.000 description 2
• 230000001747 exhibiting Effects 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• 230000031700 light absorption Effects 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 230000002194 synthesizing Effects 0.000 description 2
• WGLPBDUCMAPZCE-UHFFFAOYSA-N trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 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
• 210000001772 Blood Platelets Anatomy 0.000 description 1
• ZQXSFOAPFLRFGY-LZWHNZSHSA-N [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(4-methylanilino)-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate Chemical compound N([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)C1=CC=C(C)C=C1 ZQXSFOAPFLRFGY-LZWHNZSHSA-N 0.000 description 1
• 125000004429 atoms Chemical group 0.000 description 1
• WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
• 238000004364 calculation method Methods 0.000 description 1
• 238000007256 debromination reaction Methods 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000011343 solid material Substances 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1