CA1201712A - Carbacyclin analogs - Google Patents

Info

Publication number

CA1201712A

CA1201712A CA000368710A CA368710A CA1201712A CA 1201712 A CA1201712 A CA 1201712A CA 000368710 A CA000368710 A CA 000368710A CA 368710 A CA368710 A CA 368710A CA 1201712 A CA1201712 A CA 1201712A

Authority

CA

Canada

Prior art keywords

general formula

compound

defined above

produce

analog

Prior art date

1980-02-28

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Links

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• CIPO
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• XZFRIPGNUQRGPI-WLPVIMDJSA-N Carbacyclin Chemical class C1\C(=C\CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 XZFRIPGNUQRGPI-WLPVIMDJSA-N 0.000 title claims 27
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 42
• 239000000126 substance Substances 0.000 claims abstract description 36
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 17
• 150000001875 compounds Chemical class 0.000 claims description 482
• 238000000034 method Methods 0.000 claims description 259
• -1 tri-substituted phenoxy Chemical group 0.000 claims description 195
• 230000000875 corresponding effect Effects 0.000 claims description 111
• 239000000203 mixture Substances 0.000 claims description 101
• 230000008569 process Effects 0.000 claims description 94
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 83
• 229910052739 hydrogen Inorganic materials 0.000 claims description 82
• 239000002253 acid Substances 0.000 claims description 65
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 58
• 150000001408 amides Chemical class 0.000 claims description 57
• 150000004702 methyl esters Chemical class 0.000 claims description 53
• 125000006239 protecting group Chemical group 0.000 claims description 47
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
• 125000001424 substituent group Chemical group 0.000 claims description 36
• 125000004432 carbon atom Chemical group C* 0.000 claims description 34
• 150000002148 esters Chemical class 0.000 claims description 34
• 150000001412 amines Chemical class 0.000 claims description 31
• 150000002576 ketones Chemical class 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 29
• 229920006395 saturated elastomer Polymers 0.000 claims description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
• 150000001450 anions Chemical class 0.000 claims description 19
• 150000001768 cations Chemical class 0.000 claims description 18
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
• 238000004519 manufacturing process Methods 0.000 claims description 17
• 230000007062 hydrolysis Effects 0.000 claims description 16
• 238000006460 hydrolysis reaction Methods 0.000 claims description 16
• 230000003301 hydrolyzing effect Effects 0.000 claims description 15
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 14
• 150000003138 primary alcohols Chemical class 0.000 claims description 13
• 230000009467 reduction Effects 0.000 claims description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 12
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 230000003647 oxidation Effects 0.000 claims description 11
• 238000007254 oxidation reaction Methods 0.000 claims description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
• 150000007513 acids Chemical class 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 239000002585 base Substances 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 230000001590 oxidative effect Effects 0.000 claims description 9
• 125000005555 sulfoximide group Chemical group 0.000 claims description 9
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
• 150000003333 secondary alcohols Chemical class 0.000 claims description 7
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004344 phenylpropyl group Chemical group 0.000 claims description 5
• 125000003944 tolyl group Chemical group 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 229960000711 alprostadil Drugs 0.000 claims description 4
• 230000018044 dehydration Effects 0.000 claims description 4
• 238000006297 dehydration reaction Methods 0.000 claims description 4
• 238000010438 heat treatment Methods 0.000 claims description 4
• 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 4
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 3
• 239000007818 Grignard reagent Substances 0.000 claims description 3
• 229910052783 alkali metal Inorganic materials 0.000 claims description 3
• 150000001340 alkali metals Chemical class 0.000 claims description 3
• 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
• MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 claims description 3
• 238000005949 ozonolysis reaction Methods 0.000 claims description 3
• 229910001023 sodium amalgam Inorganic materials 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
• 125000003602 2-(3-thienyl)ethoxy group Chemical group [H]C1=C([H])C(=C([H])S1)C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 16
• RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims 4
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 3
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
• 125000004185 ester group Chemical group 0.000 claims 2
• 150000003509 tertiary alcohols Chemical class 0.000 claims 2
• 230000001131 transforming effect Effects 0.000 claims 2
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
• 125000001589 carboacyl group Chemical group 0.000 claims 1
• 229940000425 combination drug Drugs 0.000 claims 1
• XZFRIPGNUQRGPI-WBQKLGIQSA-N Carbaprostacyclin Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 XZFRIPGNUQRGPI-WBQKLGIQSA-N 0.000 abstract description 34
• 238000002360 preparation method Methods 0.000 abstract description 29
• 239000000543 intermediate Substances 0.000 abstract description 28
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 13
• 230000000144 pharmacologic effect Effects 0.000 abstract description 5
• KXYGKDBONOVZOM-UHFFFAOYSA-N 1h-cyclopenta[a]naphthalene Chemical class C1=CC=CC2=C3CC=CC3=CC=C21 KXYGKDBONOVZOM-UHFFFAOYSA-N 0.000 abstract description 2
• 230000001110 prostacyclinlike Effects 0.000 abstract description 2
• AEBWATHAIVJLTA-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene Chemical compound C1CCC2CCCC21 AEBWATHAIVJLTA-UHFFFAOYSA-N 0.000 abstract 1
• 230000002744 anti-aggregatory effect Effects 0.000 abstract 1
• 238000001311 chemical methods and process Methods 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 493
• 235000013350 formula milk Nutrition 0.000 description 404
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 344
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 184
• 229940093499 ethyl acetate Drugs 0.000 description 163
• 235000019439 ethyl acetate Nutrition 0.000 description 163
• 239000000047 product Substances 0.000 description 159
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 151
• 239000000741 silica gel Substances 0.000 description 139
• 229910002027 silica gel Inorganic materials 0.000 description 139
• 229960001866 silicon dioxide Drugs 0.000 description 139
• 230000009102 absorption Effects 0.000 description 121
• 238000010521 absorption reaction Methods 0.000 description 121
• 239000000243 solution Substances 0.000 description 115
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 109
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 103
• 239000012267 brine Substances 0.000 description 102
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
• 239000001257 hydrogen Substances 0.000 description 78
• 238000005481 NMR spectroscopy Methods 0.000 description 70
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
• 239000007795 chemical reaction product Substances 0.000 description 54
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 54
• 229960004132 diethyl ether Drugs 0.000 description 52
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
• 239000012299 nitrogen atmosphere Substances 0.000 description 49
• HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 46
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
• 238000006243 chemical reaction Methods 0.000 description 38
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 32
• 239000000725 suspension Substances 0.000 description 32
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
• 238000003756 stirring Methods 0.000 description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 28
• 230000009466 transformation Effects 0.000 description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
• 239000003921 oil Substances 0.000 description 25
• KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 25
• 238000004587 chromatography analysis Methods 0.000 description 23
• 239000012230 colorless oil Substances 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• 238000011282 treatment Methods 0.000 description 23
• 229960000583 acetic acid Drugs 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• 239000000284 extract Substances 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• 229960001123 epoprostenol Drugs 0.000 description 20
• 229960003390 magnesium sulfate Drugs 0.000 description 19
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
• 235000019341 magnesium sulphate Nutrition 0.000 description 19
• 239000002904 solvent Substances 0.000 description 19
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
• 235000011054 acetic acid Nutrition 0.000 description 17
• 235000017557 sodium bicarbonate Nutrition 0.000 description 17
• 238000001819 mass spectrum Methods 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
• 229960001407 sodium bicarbonate Drugs 0.000 description 16
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 150000008064 anhydrides Chemical class 0.000 description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 229960001701 chloroform Drugs 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 229960003010 sodium sulfate Drugs 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• 229910052799 carbon Inorganic materials 0.000 description 13
• JCSGAUKCDAVARS-SOUFLCLCSA-N chembl2106517 Chemical compound C1([C@@H](O)[C@H]2C3)=CC=CC(O)=C1C(=O)C2=C(O)[C@@]1(O)[C@@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C1=O JCSGAUKCDAVARS-SOUFLCLCSA-N 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 229960005419 nitrogen Drugs 0.000 description 13
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 150000001299 aldehydes Chemical class 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
• 238000002844 melting Methods 0.000 description 12
• 230000008018 melting Effects 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 12
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
• 125000001309 chloro group Chemical group Cl* 0.000 description 11
• 235000011118 potassium hydroxide Nutrition 0.000 description 11
• 229940093932 potassium hydroxide Drugs 0.000 description 11
• 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 description 10
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
• 230000003247 decreasing effect Effects 0.000 description 10
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 10
• 235000015424 sodium Nutrition 0.000 description 10
• 239000012312 sodium hydride Substances 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
• 239000005909 Kieselgur Substances 0.000 description 9
• 239000012300 argon atmosphere Substances 0.000 description 9
• 150000001721 carbon Chemical group 0.000 description 9
• 238000007796 conventional method Methods 0.000 description 9
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
• 238000005886 esterification reaction Methods 0.000 description 9
• 229960000443 hydrochloric acid Drugs 0.000 description 9
• 235000011167 hydrochloric acid Nutrition 0.000 description 9
• 150000002500 ions Chemical class 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 229910052708 sodium Inorganic materials 0.000 description 9
• 238000000844 transformation Methods 0.000 description 9
• DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical class C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 230000032050 esterification Effects 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 150000003180 prostaglandins Chemical class 0.000 description 8
• 150000003512 tertiary amines Chemical class 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• 125000002252 acyl group Chemical group 0.000 description 7
• 239000002024 ethyl acetate extract Substances 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 239000000376 reactant Substances 0.000 description 7
• 229940124530 sulfonamide Drugs 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 101150041968 CDC13 gene Proteins 0.000 description 6
• 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 6
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 125000003368 amide group Chemical group 0.000 description 6
• 235000019270 ammonium chloride Nutrition 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• 230000037396 body weight Effects 0.000 description 6
• 239000003795 chemical substances by application Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
• 150000002596 lactones Chemical class 0.000 description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
• JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 5
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
• 241000282414 Homo sapiens Species 0.000 description 5
• 239000003810 Jones reagent Substances 0.000 description 5
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
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