BE512962A - - Google Patents

Info

Publication number

BE512962A

BE512962A BE512962DA BE512962A BE 512962 A BE512962 A BE 512962A BE 512962D A BE512962D A BE 512962DA BE 512962 A BE512962 A BE 512962A

Authority

BE

Belgium

Prior art keywords

ene

compounds

acid

water

general formula

Prior art date

Links

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• 150000001875 compounds Chemical class 0.000 claims description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 9
• 239000002904 solvent Substances 0.000 claims description 9
• 239000000203 mixture Substances 0.000 claims description 7
• 230000015572 biosynthetic process Effects 0.000 claims description 6
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
• 239000011707 mineral Substances 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
• 239000003960 organic solvent Substances 0.000 claims description 5
• 239000007787 solid Substances 0.000 claims description 4
• 239000007858 starting material Substances 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• 238000006243 chemical reaction Methods 0.000 claims description 3
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
• 230000007062 hydrolysis Effects 0.000 claims description 2
• 238000006460 hydrolysis reaction Methods 0.000 claims description 2
• 230000001590 oxidative effect Effects 0.000 claims description 2
• 230000008707 rearrangement Effects 0.000 claims 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• 239000000047 product Substances 0.000 description 11
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• 238000002844 melting Methods 0.000 description 10
• 230000008018 melting Effects 0.000 description 10
• 229910052794 bromium Inorganic materials 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
• 235000017557 sodium bicarbonate Nutrition 0.000 description 5
• FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 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 4
• MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• 229960004544 cortisone Drugs 0.000 description 4
• 230000001747 exhibiting effect Effects 0.000 description 4
• 235000010755 mineral Nutrition 0.000 description 4
• 239000011343 solid material Substances 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 238000000354 decomposition reaction Methods 0.000 description 3
• 125000000950 dibromo group Chemical group Br* 0.000 description 3
• YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
• 238000012360 testing method Methods 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
• 125000004423 acyloxy group Chemical group 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 150000003431 steroids Chemical class 0.000 description 2
• 125000001424 substituent group Chemical group 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 239000004593 Epoxy Substances 0.000 description 1
• VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 239000002178 crystalline material Substances 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 150000002009 diols Chemical class 0.000 description 1
• 239000012153 distilled water Substances 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 238000012549 training Methods 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000005406 washing Methods 0.000 description 1