PL61040B1 - - Google Patents

Info

Publication number

PL61040B1

PL61040B1 PL116019A PL11601966A PL61040B1 PL 61040 B1 PL61040 B1 PL 61040B1 PL 116019 A PL116019 A PL 116019A PL 11601966 A PL11601966 A PL 11601966A PL 61040 B1 PL61040 B1 PL 61040B1

Authority

PL

Poland

Prior art keywords

formula

log

compound

max

group

Prior art date

1966-08-08

Links

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• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
• 125000000468 ketone group Chemical group 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 229910052708 sodium Inorganic materials 0.000 claims description 6
• 239000011734 sodium Substances 0.000 claims description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• 238000005907 ketalization reaction Methods 0.000 claims description 3
• 239000002253 acid Substances 0.000 claims description 2
• 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
• 150000001875 compounds Chemical class 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000000243 solution Substances 0.000 description 9
• 238000002844 melting Methods 0.000 description 8
• 230000008018 melting Effects 0.000 description 8
• 150000002576 ketones Chemical class 0.000 description 7
• 239000000047 product Substances 0.000 description 6
• 125000003118 aryl group Chemical group 0.000 description 5
• 230000009467 reduction Effects 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 238000010521 absorption reaction Methods 0.000 description 4
• 239000005556 hormone Substances 0.000 description 4
• 229940088597 hormone Drugs 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• 238000002329 infrared spectrum Methods 0.000 description 2
• 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 description 2
• DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
• 235000009754 Vitis X bourquina Nutrition 0.000 description 1
• 235000012333 Vitis X labruscana Nutrition 0.000 description 1
• 240000006365 Vitis vinifera Species 0.000 description 1
• 235000014787 Vitis vinifera Nutrition 0.000 description 1
• 239000006096 absorbing agent Substances 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 210000004404 adrenal cortex Anatomy 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 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
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
• 239000000538 analytical sample Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 150000001491 aromatic compounds Chemical class 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• PDRGHUMCVRDZLQ-UHFFFAOYSA-N d-equilenin Natural products OC1=CC=C2C(CCC3(C4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-UHFFFAOYSA-N 0.000 description 1
• 230000008034 disappearance Effects 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• PDRGHUMCVRDZLQ-WMZOPIPTSA-N equilenin Chemical compound OC1=CC=C2C(CC[C@]3([C@H]4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-WMZOPIPTSA-N 0.000 description 1
• 229960003399 estrone Drugs 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 230000003054 hormonal effect Effects 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 238000002211 ultraviolet spectrum Methods 0.000 description 1