PL81913B1 - - Google Patents

Info

Publication number

PL81913B1

PL81913B1 PL14968371A PL14968371A PL81913B1 PL 81913 B1 PL81913 B1 PL 81913B1 PL 14968371 A PL14968371 A PL 14968371A PL 14968371 A PL14968371 A PL 14968371A PL 81913 B1 PL81913 B1 PL 81913B1

Authority

PL

Poland

Prior art keywords

general formula

compound

starting material

carbon atoms

acid anhydride

Prior art date

1970-07-29

Links

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• 238000000034 method Methods 0.000 claims description 33
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
• 150000001875 compounds Chemical class 0.000 claims description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
• 229910052740 iodine Inorganic materials 0.000 claims description 16
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
• 239000011630 iodine Substances 0.000 claims description 14
• 239000000203 mixture Substances 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 238000006243 chemical reaction Methods 0.000 claims description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 239000003054 catalyst Substances 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 239000002904 solvent Substances 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 150000007524 organic acids Chemical class 0.000 claims description 6
• 230000010933 acylation Effects 0.000 claims description 5
• 238000005917 acylation reaction Methods 0.000 claims description 5
• 125000000746 allylic group Chemical group 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• -1 3-methyl-androst-4-ene Chemical compound 0.000 claims description 4
• 150000008065 acid anhydrides Chemical class 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• 239000003795 chemical substances by application Substances 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 239000007858 starting material Substances 0.000 claims 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
• ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 claims 1
• LRJOMUJRLNCICJ-JZYPGELDSA-N Prednisolone acetate Chemical group C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O LRJOMUJRLNCICJ-JZYPGELDSA-N 0.000 claims 1
• FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
• VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
• 229910052739 hydrogen Inorganic materials 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 9
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 238000003756 stirring Methods 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• 238000000921 elemental analysis Methods 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 4
• 239000003638 chemical reducing agent Substances 0.000 description 4
• 150000001993 dienes Chemical class 0.000 description 4
• 239000005457 ice water Substances 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 230000008018 melting Effects 0.000 description 4
• 230000007935 neutral effect Effects 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 229910000029 sodium carbonate Inorganic materials 0.000 description 4
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
• 235000019345 sodium thiosulphate Nutrition 0.000 description 4
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• 229960000583 acetic acid Drugs 0.000 description 3
• 230000021736 acetylation Effects 0.000 description 3
• 238000006640 acetylation reaction Methods 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 238000007086 side reaction Methods 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 description 2
• 239000002244 precipitate Substances 0.000 description 2
• 239000001632 sodium acetate Substances 0.000 description 2
• 235000017281 sodium acetate Nutrition 0.000 description 2
• 150000003431 steroids Chemical class 0.000 description 2
• BUCJHJXFXUZJHL-UHFFFAOYSA-N 1-ethylcyclohexan-1-ol Chemical compound CCC1(O)CCCCC1 BUCJHJXFXUZJHL-UHFFFAOYSA-N 0.000 description 1
• RFZHJHSNHYIRNE-UHFFFAOYSA-N 2,3-dimethylpentan-3-ol Chemical compound CCC(C)(O)C(C)C RFZHJHSNHYIRNE-UHFFFAOYSA-N 0.000 description 1
• WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 1
• HVPGGLNDHUWMLS-UHFFFAOYSA-N 3,6-dimethylheptan-3-ol Chemical compound CCC(C)(O)CCC(C)C HVPGGLNDHUWMLS-UHFFFAOYSA-N 0.000 description 1
• WNDLTOTUHMHNOC-UHFFFAOYSA-N 3-ethylhexan-3-ol Chemical compound CCCC(O)(CC)CC WNDLTOTUHMHNOC-UHFFFAOYSA-N 0.000 description 1
• XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 description 1
• FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 1
• KYWJZCSJMOILIZ-UHFFFAOYSA-N 3-methylhexan-3-ol Chemical compound CCCC(C)(O)CC KYWJZCSJMOILIZ-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• IMONTRJLAWHYGT-ZCPXKWAGSA-N Norethindrone Acetate Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](C#C)(OC(=O)C)[C@@]1(C)CC2 IMONTRJLAWHYGT-ZCPXKWAGSA-N 0.000 description 1
• 239000004133 Sodium thiosulphate Substances 0.000 description 1
• CCKIUJJSFRKLBO-VNIVASGNSA-N [(8r,9s,10r,13r,14s)-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-13-yl]methanediol Chemical compound C1CC2=CCCC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C(O)O)CC2 CCKIUJJSFRKLBO-VNIVASGNSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 150000002009 diols Chemical class 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000012259 ether extract Substances 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 230000003054 hormonal effect Effects 0.000 description 1
• 239000001257 hydrogen Substances 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 229960001652 norethindrone acetate Drugs 0.000 description 1
• TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical group O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
• WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 230000003637 steroidlike Effects 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1