NO750765L - - Google Patents

Info

Publication number

NO750765L

NO750765L NO750765A NO750765A NO750765L NO 750765 L NO750765 L NO 750765L NO 750765 A NO750765 A NO 750765A NO 750765 A NO750765 A NO 750765A NO 750765 L NO750765 L NO 750765L

Authority

NO

Norway

Prior art keywords

group

formula

denotes

acid

residue

Prior art date

1974-07-12

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• -1 3-cephem compound Chemical class 0.000 claims description 355
• 150000001875 compounds Chemical class 0.000 claims description 144
• 125000003277 amino group Chemical group 0.000 claims description 139
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 108
• 239000002253 acid Substances 0.000 claims description 101
• 150000003839 salts Chemical class 0.000 claims description 91
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 81
• 238000000034 method Methods 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 71
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
• 238000006243 chemical reaction Methods 0.000 claims description 38
• 239000007858 starting material Substances 0.000 claims description 38
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 37
• 239000003795 chemical substances by application Substances 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 239000002585 base Substances 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 28
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
• 238000005917 acylation reaction Methods 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 230000010933 acylation Effects 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
• 239000000203 mixture Substances 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 125000000524 functional group Chemical group 0.000 claims description 23
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• 239000000126 substance Substances 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 125000002252 acyl group Chemical group 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 229910052783 alkali metal Inorganic materials 0.000 claims description 21
• 239000003153 chemical reaction reagent Substances 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 150000008064 anhydrides Chemical class 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000006239 protecting group Chemical group 0.000 claims description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
• 239000003638 chemical reducing agent Substances 0.000 claims description 19
• 239000000460 chlorine Substances 0.000 claims description 19
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 150000007513 acids Chemical class 0.000 claims description 17
• 125000001931 aliphatic group Chemical group 0.000 claims description 17
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
• 150000002148 esters Chemical class 0.000 claims description 16
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 15
• FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
• 230000000269 nucleophilic effect Effects 0.000 claims description 12
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 12
• 150000001340 alkali metals Chemical class 0.000 claims description 11
• 125000002947 alkylene group Chemical group 0.000 claims description 11
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
• 125000001453 quaternary ammonium group Chemical group 0.000 claims description 11
• 239000011541 reaction mixture Substances 0.000 claims description 11
• 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 11
• 239000005864 Sulphur Substances 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
• 150000007530 organic bases Chemical class 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000004423 acyloxy group Chemical group 0.000 claims description 9
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• 125000005110 aryl thio group Chemical group 0.000 claims description 9
• 150000002430 hydrocarbons Chemical group 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• 150000003973 alkyl amines Chemical class 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000005002 aryl methyl group Chemical group 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 239000000543 intermediate Substances 0.000 claims description 8
• 239000012433 hydrogen halide Substances 0.000 claims description 7
• 229910000039 hydrogen halide Inorganic materials 0.000 claims description 7
• 229910052744 lithium Inorganic materials 0.000 claims description 7
• 239000000047 product Substances 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
• 150000001735 carboxylic acids Chemical class 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 5
• 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 5
• 125000000369 oxido group Chemical group [*]=O 0.000 claims description 5
• 239000004332 silver Substances 0.000 claims description 5
• 238000003797 solvolysis reaction Methods 0.000 claims description 5
• 239000002262 Schiff base Substances 0.000 claims description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
• WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 claims description 4
• 229910052709 silver Inorganic materials 0.000 claims description 4
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
• 239000005711 Benzoic acid Substances 0.000 claims description 2
• 150000004753 Schiff bases Chemical class 0.000 claims description 2
• 125000005237 alkyleneamino group Chemical group 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 235000010233 benzoic acid Nutrition 0.000 claims description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
• 150000002009 diols Chemical class 0.000 claims description 2
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
• 229940100892 mercury compound Drugs 0.000 claims description 2
• 150000002731 mercury compounds Chemical class 0.000 claims description 2
• 229910000474 mercury oxide Inorganic materials 0.000 claims description 2
• UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 2
• 125000002524 organometallic group Chemical group 0.000 claims description 2
• 230000001590 oxidative effect Effects 0.000 claims description 2
• 229920000642 polymer Polymers 0.000 claims description 2
• 229940100890 silver compound Drugs 0.000 claims description 2
• 229910001923 silver oxide Inorganic materials 0.000 claims description 2
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 3
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims 1
• SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims 1
• 125000004430 oxygen atom Chemical group O* 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• 239000000243 solution Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• 239000002904 solvent Substances 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 150000004820 halides Chemical class 0.000 description 14
• 239000011261 inert gas Substances 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• 238000001816 cooling Methods 0.000 description 13
• 238000010438 heat treatment Methods 0.000 description 13
• 229910052751 metal Inorganic materials 0.000 description 13
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
• 230000007062 hydrolysis Effects 0.000 description 12
• 238000006460 hydrolysis reaction Methods 0.000 description 12
• 239000002184 metal Substances 0.000 description 12
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• 239000003085 diluting agent Substances 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
• 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
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 239000012298 atmosphere Substances 0.000 description 10
• 238000003776 cleavage reaction Methods 0.000 description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
• 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 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 9
• 235000019253 formic acid Nutrition 0.000 description 9
• 230000007017 scission Effects 0.000 description 9
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 229910052794 bromium Inorganic materials 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• 229910052698 phosphorus Inorganic materials 0.000 description 8
• 230000002829 reductive effect Effects 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 8
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 7
• 239000012445 acidic reagent Substances 0.000 description 7
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 7
• 150000002736 metal compounds Chemical class 0.000 description 7
• 150000007522 mineralic acids Chemical class 0.000 description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 7
• 238000006722 reduction reaction Methods 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
• 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 6
• 150000003863 ammonium salts Chemical class 0.000 description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
• 229910052500 inorganic mineral Inorganic materials 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• 235000010755 mineral Nutrition 0.000 description 6
• 239000011707 mineral Substances 0.000 description 6
• 231100000252 nontoxic Toxicity 0.000 description 6
• 230000003000 nontoxic effect Effects 0.000 description 6
• 239000012434 nucleophilic reagent Substances 0.000 description 6
• 125000003431 oxalo group Chemical group 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• 239000011574 phosphorus Substances 0.000 description 6
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
• 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 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 125000004442 acylamino group Chemical group 0.000 description 5
• 239000003513 alkali Substances 0.000 description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 238000000338 in vitro Methods 0.000 description 5
• 229910052742 iron Inorganic materials 0.000 description 5
• 150000002576 ketones Chemical class 0.000 description 5
• JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 239000000825 pharmaceutical preparation Substances 0.000 description 5
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 5
• 239000011780 sodium chloride Substances 0.000 description 5
• IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 5
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
• 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 description 5
• 229910052725 zinc Inorganic materials 0.000 description 5
• 239000011701 zinc Substances 0.000 description 5
• 241000894006 Bacteria Species 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
• YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
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• WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
• JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1