CA1206968A

CA1206968A - 2-oxoazetidine derivatives, their production and use

2-oxoazetidine derivatives, their production and use

Info

Publication number: CA1206968A
Authority: CA; Canada
Prior art keywords: group; amino; azetidinone; acetyl; process according
Prior art date: 1982-05-31
Legal status : Expired

Application number

CA000429158A

Other languages

English (en)

French (fr)

Inventor

Michihiko Ochiai

Taisuke Matsuo, (Deceased)

Current Assignee

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date

1982-05-31

Filing date

1983-05-30

Publication date

1986-07-02

1983-05-30 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1986-07-02 Application granted granted Critical

1986-07-02 Publication of CA1206968A publication Critical patent/CA1206968A/en

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract description 4
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title description 5
-1 methoxyl group Chemical group 0.000 claims abstract description 534
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 143
150000001875 compounds Chemical class 0.000 claims abstract description 102
150000003839 salts Chemical class 0.000 claims abstract description 99
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 89
125000000217 alkyl group Chemical group 0.000 claims abstract description 73
125000003277 amino group Chemical group 0.000 claims abstract description 65
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 62
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 39
150000002148 esters Chemical group 0.000 claims abstract description 32
125000002947 alkylene group Chemical group 0.000 claims abstract description 30
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 23
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 17
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 14
125000004450 alkenylene group Chemical group 0.000 claims abstract description 12
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims abstract description 11
125000002393 azetidinyl group Chemical group 0.000 claims abstract description 11
125000004423 acyloxy group Chemical group 0.000 claims abstract description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims abstract description 9
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 187
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 159
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 149
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 108
239000000203 mixture Substances 0.000 claims description 80
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
239000000047 product Substances 0.000 claims description 59
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 38
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
229910052717 sulfur Inorganic materials 0.000 claims description 36
125000001841 imino group Chemical group [H]N=* 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000006239 protecting group Chemical group 0.000 claims description 29
125000002252 acyl group Chemical group 0.000 claims description 27
239000007858 starting material Substances 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000005518 carboxamido group Chemical group 0.000 claims description 24
239000000126 substance Substances 0.000 claims description 24
238000006277 sulfonation reaction Methods 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
238000005917 acylation reaction Methods 0.000 claims description 12
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 11
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
125000004193 piperazinyl group Chemical group 0.000 claims description 9
239000011593 sulfur Chemical group 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
125000001425 triazolyl group Chemical group 0.000 claims description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
230000010933 acylation Effects 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 5
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
125000003831 tetrazolyl group Chemical group 0.000 claims description 5
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
239000003456 ion exchange resin Substances 0.000 claims description 4
229920003303 ion-exchange polymer Polymers 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 3
125000005596 alkyl carboxamido group Chemical group 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229960003424 phenylacetic acid Drugs 0.000 claims description 3
239000003279 phenylacetic acid Substances 0.000 claims description 3
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 2
125000002828 maloyl group Chemical group C(C(O)CC(=O)*)(=O)* 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 2
125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
159000000000 sodium salts Chemical group 0.000 claims 15
WGBMNHUQXMFODO-UHFFFAOYSA-M sodium;n-(methylamino)carbamodithioate Chemical compound [Na+].CNNC([S-])=S WGBMNHUQXMFODO-UHFFFAOYSA-M 0.000 claims 9
VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 claims 3
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
STRHCGASRRVXTO-PSASIEDQSA-N 2-chloro-n-[4-[[[2-oxo-2-[[(3r,4r)-2-oxo-4-sulfamoylazetidin-3-yl]amino]ethylidene]amino]oxymethyl]-1,3-thiazol-2-yl]acetamide Chemical compound NS(=O)(=O)[C@H]1NC(=O)[C@H]1NC(=O)C=NOCC1=CSC(NC(=O)CCl)=N1 STRHCGASRRVXTO-PSASIEDQSA-N 0.000 claims 1
DMRZWYZHPZMZJQ-STQMWFEESA-N ethyl 3-[(2s,3s)-3-[[2-[[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]methoxyimino]acetyl]amino]-4-oxoazetidin-2-yl]triazole-4-carboxylate Chemical compound CCOC(=O)C1=CN=NN1[C@H]1[C@H](NC(=O)C=NOCC=2N=C(NC(=O)CCl)SC=2)C(=O)N1 DMRZWYZHPZMZJQ-STQMWFEESA-N 0.000 claims 1
238000007327 hydrogenolysis reaction Methods 0.000 claims 1
DWHXUFRYVGVIJX-NWDGAFQWSA-N methyl 3-[(2r,3s)-3-[[2-[[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]methoxyimino]acetyl]amino]-4-oxoazetidin-2-yl]triazole-4-carboxylate Chemical compound COC(=O)C1=CN=NN1[C@@H]1[C@H](NC(=O)C=NOCC=2N=C(NC(=O)CCl)SC=2)C(=O)N1 DWHXUFRYVGVIJX-NWDGAFQWSA-N 0.000 claims 1
ARYPAVHVOFRARA-UHFFFAOYSA-N n-[2-[4-oxo-3-(tritylamino)azetidin-2-yl]sulfanylethyl]acetamide Chemical compound CC(=O)NCCSC1NC(=O)C1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ARYPAVHVOFRARA-UHFFFAOYSA-N 0.000 claims 1
150000003462 sulfoxides Chemical group 0.000 claims 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
230000000845 anti-microbial effect Effects 0.000 abstract description 5
230000002401 inhibitory effect Effects 0.000 abstract description 5
241000894006 Bacteria Species 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
208000035473 Communicable disease Diseases 0.000 abstract description 2
241000124008 Mammalia Species 0.000 abstract description 2
125000001589 carboacyl group Chemical group 0.000 abstract 1
230000000069 prophylactic effect Effects 0.000 abstract 1
229940124597 therapeutic agent Drugs 0.000 abstract 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 154
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 89
239000000243 solution Substances 0.000 description 86
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
239000011734 sodium Substances 0.000 description 57
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 56
229910052708 sodium Inorganic materials 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
230000002829 reductive effect Effects 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 41
239000000460 chlorine Substances 0.000 description 39
125000000623 heterocyclic group Chemical group 0.000 description 37
239000002904 solvent Substances 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
238000001816 cooling Methods 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
239000011347 resin Substances 0.000 description 26
229920005989 resin Polymers 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
238000010898 silica gel chromatography Methods 0.000 description 17
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000000706 filtrate Substances 0.000 description 14
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 12
ONPGOSVDVDPBCY-CQSZACIVSA-N 6-amino-5-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-n-[4-(4-methylpiperazine-1-carbonyl)phenyl]pyridazine-3-carboxamide Chemical compound O([C@H](C)C=1C(=C(F)C=CC=1Cl)Cl)C(C(=NN=1)N)=CC=1C(=O)NC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 ONPGOSVDVDPBCY-CQSZACIVSA-N 0.000 description 11
238000001914 filtration Methods 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
125000004430 oxygen atom Chemical group O* 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
229920001467 poly(styrenesulfonates) Polymers 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 9
239000000843 powder Substances 0.000 description 9
101150041968 CDC13 gene Proteins 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
239000010410 layer Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
229940086542 triethylamine Drugs 0.000 description 8
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
125000002373 5 membered heterocyclic group Chemical group 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 6
239000002585 base Substances 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
239000002198 insoluble material Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
239000012346 acetyl chloride Substances 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
HYGYSIDIKIGPJA-UHFFFAOYSA-N chloroform;ethyl acetate;methanol Chemical compound OC.ClC(Cl)Cl.CCOC(C)=O HYGYSIDIKIGPJA-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
230000008030 elimination Effects 0.000 description 5
238000003379 elimination reaction Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
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