FI66389C - Foerfarande foer framstaellning av 7beta-amino-2- eller -3-cefem-3-ol-4-karboxylsyrafoereningar - Google Patents

Info

Publication number

FI66389C

FI66389C FI750503A FI750503A FI66389C FI 66389 C FI66389 C FI 66389C FI 750503 A FI750503 A FI 750503A FI 750503 A FI750503 A FI 750503A FI 66389 C FI66389 C FI 66389C

Authority

FI

Finland

Prior art keywords

acid

group

phenoxyacetamido

formula

cephem

Prior art date

1974-02-26

Links

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• Global Dossier
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• 238000005057 refrigeration Methods 0.000 title 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 508
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 408
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 321
• -1 hydroxychlorophenyl Chemical group 0.000 claims description 293
• 239000000203 mixture Substances 0.000 claims description 181
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 125
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 121
• 150000001875 compounds Chemical class 0.000 claims description 121
• 239000000741 silica gel Substances 0.000 claims description 111
• 229910002027 silica gel Inorganic materials 0.000 claims description 111
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 78
• 150000003839 salts Chemical class 0.000 claims description 59
• 238000006243 chemical reaction Methods 0.000 claims description 54
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 46
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 43
• 238000000862 absorption spectrum Methods 0.000 claims description 39
• FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
• 239000003795 chemical substances by application Substances 0.000 claims description 22
• SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims description 21
• 125000002252 acyl group Chemical group 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 238000000034 method Methods 0.000 claims description 20
• 150000002148 esters Chemical class 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
• 238000010438 heat treatment Methods 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 239000011261 inert gas Substances 0.000 claims description 15
• 239000011630 iodine Substances 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 14
• 239000012442 inert solvent Substances 0.000 claims description 11
• 230000003647 oxidation Effects 0.000 claims description 10
• 238000007254 oxidation reaction Methods 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 229920002472 Starch Polymers 0.000 claims description 8
• 239000012298 atmosphere Substances 0.000 claims description 8
• 238000006266 etherification reaction Methods 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 230000007062 hydrolysis Effects 0.000 claims description 8
• 238000006460 hydrolysis reaction Methods 0.000 claims description 8
• 230000032050 esterification Effects 0.000 claims description 7
• 238000005886 esterification reaction Methods 0.000 claims description 7
• 150000003949 imides Chemical class 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 239000008107 starch Substances 0.000 claims description 7
• KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 239000004305 biphenyl Chemical group 0.000 claims description 5
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 235000019698 starch Nutrition 0.000 claims description 5
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 125000006267 biphenyl group Chemical group 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical group N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 238000007127 saponification reaction Methods 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
• 239000007789 gas Substances 0.000 claims description 2
• 150000002357 guanidines Chemical class 0.000 claims description 2
• 238000009472 formulation Methods 0.000 claims 4
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
• CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical group N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 claims 1
• ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
• 150000001782 cephems Chemical class 0.000 claims 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
• 239000000243 solution Substances 0.000 description 207
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 200
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 130
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 114
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 93
• 239000002253 acid Substances 0.000 description 88
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 71
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• 238000002329 infrared spectrum Methods 0.000 description 65
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
• 235000019441 ethanol Nutrition 0.000 description 56
• 238000003756 stirring Methods 0.000 description 55
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
• 239000002904 solvent Substances 0.000 description 53
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 51
• 239000010410 layer Substances 0.000 description 51
• 229910052938 sodium sulfate Inorganic materials 0.000 description 45
• 235000011152 sodium sulphate Nutrition 0.000 description 45
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 43
• 239000007858 starting material Substances 0.000 description 42
• 229960000583 acetic acid Drugs 0.000 description 40
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 39
• 238000002844 melting Methods 0.000 description 38
• 230000008018 melting Effects 0.000 description 38
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
• 239000012074 organic phase Substances 0.000 description 37
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 36
• 229910052757 nitrogen Inorganic materials 0.000 description 36
• 235000017557 sodium bicarbonate Nutrition 0.000 description 36
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 35
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 34
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 30
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
• 239000002244 precipitate Substances 0.000 description 28
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 27
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 26
• 238000001816 cooling Methods 0.000 description 25
• 125000001931 aliphatic group Chemical group 0.000 description 24
• 150000007513 acids Chemical class 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 23
• 239000011541 reaction mixture Substances 0.000 description 22
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 20
• 239000008346 aqueous phase Substances 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• 238000004587 chromatography analysis Methods 0.000 description 20
• 239000012299 nitrogen atmosphere Substances 0.000 description 20
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 19
• HSELDYLLAXROOZ-MBXJOHMKSA-N benzhydryl (z)-but-2-enoate Chemical compound C=1C=CC=CC=1C(OC(=O)\C=C/C)C1=CC=CC=C1 HSELDYLLAXROOZ-MBXJOHMKSA-N 0.000 description 19
• 239000000047 product Substances 0.000 description 19
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 18
• 239000000460 chlorine Substances 0.000 description 18
• 239000011780 sodium chloride Substances 0.000 description 18
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 17
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• 229910001385 heavy metal Inorganic materials 0.000 description 16
• YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 15
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 238000002211 ultraviolet spectrum Methods 0.000 description 15
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 14
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
• 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 12
• 150000008064 anhydrides Chemical group 0.000 description 12
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 12
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
• 239000006260 foam Substances 0.000 description 12
• 235000019253 formic acid Nutrition 0.000 description 12
• 235000015424 sodium Nutrition 0.000 description 12
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
• 238000005917 acylation reaction Methods 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 239000012043 crude product Substances 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
• CPXGFFUFUXXZGC-UHFFFAOYSA-M silver;4-methylbenzenesulfinate Chemical compound [Ag+].CC1=CC=C(S([O-])=O)C=C1 CPXGFFUFUXXZGC-UHFFFAOYSA-M 0.000 description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 10
• 125000003277 amino group Chemical group 0.000 description 10
• JYBFYDOVDDHVMZ-QFMPWRQOSA-N benzhydryl (e)-3-hydroxy-2-[2-(4-methylphenyl)sulfonylsulfanyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]but-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(=C(O)/C)/N(C(C1NC(=O)COC=2C=CC=CC=2)=O)C1SS(=O)(=O)C1=CC=C(C)C=C1 JYBFYDOVDDHVMZ-QFMPWRQOSA-N 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 239000003638 chemical reducing agent Substances 0.000 description 10
• 238000001704 evaporation Methods 0.000 description 10
• 229910052751 metal Inorganic materials 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 10
• LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 10
• 230000010933 acylation Effects 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• 239000003480 eluent Substances 0.000 description 9
• 230000008020 evaporation Effects 0.000 description 9
• 125000000524 functional group Chemical group 0.000 description 9
• 239000012362 glacial acetic acid Substances 0.000 description 9
• 239000002184 metal Substances 0.000 description 9
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 239000011877 solvent mixture Substances 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• 239000011572 manganese Substances 0.000 description 8
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
• 238000004809 thin layer chromatography Methods 0.000 description 8
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
• 229910052783 alkali metal Inorganic materials 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• NYBNBJUAHGUHSR-WGPBWIAQSA-N benzhydryl (e)-3-methoxy-2-[2-(4-methylphenyl)sulfonylsulfanyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]but-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)OC(=O)C(=C(C)/OC)\N(C(C1NC(=O)COC=2C=CC=CC=2)=O)C1SS(=O)(=O)C1=CC=C(C)C=C1 NYBNBJUAHGUHSR-WGPBWIAQSA-N 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 229910052802 copper Inorganic materials 0.000 description 7
• 239000010949 copper Substances 0.000 description 7
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
• 150000004820 halides Chemical class 0.000 description 7
• 150000008282 halocarbons Chemical class 0.000 description 7
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 7
• 150000007522 mineralic acids Chemical class 0.000 description 7
• 150000007530 organic bases Chemical class 0.000 description 7
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 7
• 239000003208 petroleum Substances 0.000 description 7
• 229910052698 phosphorus Inorganic materials 0.000 description 7
• 239000011574 phosphorus Substances 0.000 description 7
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
• 230000035484 reaction time Effects 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• WKRPOKPGPPVDPN-UHFFFAOYSA-N (4-nitrophenyl)methyl 3-methyl-2-[2-(4-methylphenyl)sulfonylsulfanyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]but-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C(C1NC(=O)COC=2C=CC=CC=2)=O)C1SS(=O)(=O)C1=CC=C(C)C=C1 WKRPOKPGPPVDPN-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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