BE568015A - - Google Patents

Info

Publication number

BE568015A

BE568015A BE568015DA BE568015A BE 568015 A BE568015 A BE 568015A BE 568015D A BE568015D A BE 568015DA BE 568015 A BE568015 A BE 568015A

Authority

BE

Belgium

Prior art keywords

methyl

dione

pregnan

alpha

acetate

Prior art date

Links

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• 238000000034 method Methods 0.000 claims description 8
• 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
• 229940045803 cuprous chloride Drugs 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 239000007818 Grignard reagent Substances 0.000 claims description 2
• 150000004795 grignard reagents Chemical class 0.000 claims description 2
• 230000003301 hydrolyzing effect Effects 0.000 claims description 2
• VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 claims description 2
• ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• 239000000243 solution Substances 0.000 description 7
• 150000001875 compounds Chemical class 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 239000000203 mixture Substances 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• 239000011541 reaction mixture Substances 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 125000002252 acyl group Chemical group 0.000 description 1
• PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 230000003444 anaesthetic effect Effects 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• -1 steroid compounds Chemical class 0.000 description 1