BE636005A - - Google Patents

Info

Publication number

BE636005A

BE636005A BE636005DA BE636005A BE 636005 A BE636005 A BE 636005A BE 636005D A BE636005D A BE 636005DA BE 636005 A BE636005 A BE 636005A

Authority

BE

Belgium

Prior art keywords

derivative

methanol

crystallization

obtaining

irehline

Prior art date

Links

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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
• 238000002425 crystallisation Methods 0.000 description 7
• 230000008025 crystallization Effects 0.000 description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 229930013930 alkaloid Natural products 0.000 description 6
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 5
• ALQAUMHHCJMVID-LQOGWUMHSA-N chembl2262637 Chemical compound C1[C@@H](N)CC[C@]2(C)[C@H]3CC[C@@]45C=N[C@@H](C)[C@H]5CC[C@H]4[C@@H]3CC=C21 ALQAUMHHCJMVID-LQOGWUMHSA-N 0.000 description 5
• 239000000203 mixture Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 244000048879 Funtumia elastica Species 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 150000003797 alkaloid derivatives Chemical class 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 238000000034 method Methods 0.000 description 3
• 238000005303 weighing Methods 0.000 description 3
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• XDELLWIDOQOKHV-UHFFFAOYSA-N (3alpha,20R)- Pregna-1,4,20-trien-3-one Natural products C1C=C2CC(N)CCC2(C)C2C1C1CCC(C(N)C)C1(C)CC2 XDELLWIDOQOKHV-UHFFFAOYSA-N 0.000 description 1
• XDELLWIDOQOKHV-YZXCLFAISA-N (3s,8s,9s,10r,13s,14s,17s)-17-[(1s)-1-aminoethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-amine Chemical compound C1C=C2C[C@@H](N)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](N)C)[C@@]1(C)CC2 XDELLWIDOQOKHV-YZXCLFAISA-N 0.000 description 1
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 229930193237 Irehdiamine Natural products 0.000 description 1
• MTTRNPRLWQGKCB-UHFFFAOYSA-N Irehdiamine B Natural products C12CCC3(C)C(C(C)N)CCC3C2CC=C2C1(C)CCC(NC)C2 MTTRNPRLWQGKCB-UHFFFAOYSA-N 0.000 description 1
• 241000283283 Orcinus orca Species 0.000 description 1
• BLAKAEFIFWAFGH-UHFFFAOYSA-N acetyl acetate;pyridine Chemical compound C1=CC=NC=C1.CC(=O)OC(C)=O BLAKAEFIFWAFGH-UHFFFAOYSA-N 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 150000001768 cations Chemical class 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 238000002360 preparation method Methods 0.000 description 1
• 150000003141 primary amines Chemical group 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 229960003387 progesterone Drugs 0.000 description 1
• 239000000186 progesterone Substances 0.000 description 1
• 238000000197 pyrolysis Methods 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
• 229930003352 steroid alkaloid Natural products 0.000 description 1
• 230000003637 steroidlike Effects 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 210000003462 vein Anatomy 0.000 description 1