DD215551A5

DD215551A5 - Verfahren zur herstellung von 6-hydroxyniederalkyl-penem-verbindungen

Verfahren zur herstellung von 6-hydroxyniederalkyl-penem-verbindungen Download PDF

Info

Publication number: DD215551A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compounds; lower alkyl; radical; compound
Prior art date: 1982-11-16

Application number

DD83256670A

Other languages

German (de)

English (en)

Inventor

Marc Lang

Original Assignee

Ciba Geigy Ag

Priority date

1982-11-16

Filing date

1983-11-14

Publication date

1984-11-14

1983-11-14 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1984-11-14 Publication of DD215551A5 publication Critical patent/DD215551A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
-1 lower alkalnoylamino Chemical group 0.000 claims abstract description 272
150000001875 compounds Chemical class 0.000 claims abstract description 261
125000000217 alkyl group Chemical group 0.000 claims abstract description 104
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 101
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 95
238000000034 method Methods 0.000 claims abstract description 67
150000003839 salts Chemical class 0.000 claims abstract description 65
239000000203 mixture Substances 0.000 claims abstract description 55
239000003795 chemical substances by application Substances 0.000 claims abstract description 40
125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
230000008569 process Effects 0.000 claims abstract description 28
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 26
229910052736 halogen Inorganic materials 0.000 claims abstract description 26
150000002367 halogens Chemical class 0.000 claims abstract description 25
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
230000003287 optical effect Effects 0.000 claims abstract description 23
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
125000000524 functional group Chemical group 0.000 claims abstract description 15
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 14
150000001768 cations Chemical class 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims abstract description 11
125000004423 acyloxy group Chemical group 0.000 claims abstract description 10
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
239000011574 phosphorus Substances 0.000 claims abstract description 10
230000004962 physiological condition Effects 0.000 claims abstract description 10
239000001301 oxygen Substances 0.000 claims abstract description 9
229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
150000002894 organic compounds Chemical class 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
125000000369 oxido group Chemical group [*]=O 0.000 claims abstract description 5
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims description 32
125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 claims description 23
125000003277 amino group Chemical group 0.000 claims description 17
239000012442 inert solvent Substances 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
238000010438 heat treatment Methods 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000000825 pharmaceutical preparation Substances 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 8
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
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 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
150000003536 tetrazoles Chemical class 0.000 claims description 4
125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 2
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 2
ZQYUYUNGKXMWPF-WRWORJQWSA-N (5r,6s)-6-(hydroxymethyl)-7-oxo-3-[4-(tetrazol-1-yl)butyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S([C@@H]1[C@H](C(N1C=1C(O)=O)=O)CO)C=1CCCCN1C=NN=N1 ZQYUYUNGKXMWPF-WRWORJQWSA-N 0.000 claims 1
208000027418 Wounds and injury Diseases 0.000 claims 1
229910001413 alkali metal ion Inorganic materials 0.000 claims 1
230000006378 damage Effects 0.000 claims 1
208000014674 injury Diseases 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 abstract description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 8
125000005237 alkyleneamino group Chemical group 0.000 abstract description 6
125000005236 alkanoylamino group Chemical group 0.000 abstract description 5
150000001450 anions Chemical class 0.000 abstract description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 2
239000005864 Sulphur Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 168
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 118
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 103
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
238000006243 chemical reaction Methods 0.000 description 57
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
239000002253 acid Substances 0.000 description 55
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 45
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
150000003254 radicals Chemical class 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
239000007858 starting material Substances 0.000 description 37
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
239000000741 silica gel Substances 0.000 description 26
229910002027 silica gel Inorganic materials 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
229910052783 alkali metal Inorganic materials 0.000 description 22
239000002585 base Substances 0.000 description 19
150000002148 esters Chemical class 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
150000001340 alkali metals Chemical class 0.000 description 18
125000006239 protecting group Chemical group 0.000 description 18
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
235000015424 sodium Nutrition 0.000 description 18
239000002904 solvent Substances 0.000 description 18
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 17
239000000460 chlorine Substances 0.000 description 17
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
238000004809 thin layer chromatography Methods 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
150000007513 acids Chemical class 0.000 description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
229910052794 bromium Inorganic materials 0.000 description 12
229910052801 chlorine Inorganic materials 0.000 description 12
239000011734 sodium Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 10
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
239000003480 eluent Substances 0.000 description 9
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
125000002252 acyl group Chemical group 0.000 description 8
125000005103 alkyl silyl group Chemical group 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
159000000000 sodium salts Chemical class 0.000 description 8
238000003797 solvolysis reaction Methods 0.000 description 8
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 8
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
241000191967 Staphylococcus aureus Species 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
238000003776 cleavage reaction Methods 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
230000009467 reduction Effects 0.000 description 7
230000007017 scission Effects 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 7
238000007920 subcutaneous administration Methods 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
238000006136 alcoholysis reaction Methods 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
229910052784 alkaline earth metal Inorganic materials 0.000 description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
239000012039 electrophile Substances 0.000 description 6
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
239000013543 active substance Substances 0.000 description 5
150000001335 aliphatic alkanes Chemical class 0.000 description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
239000012267 brine Substances 0.000 description 5
150000004649 carbonic acid derivatives Chemical class 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
238000002955 isolation Methods 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
230000000269 nucleophilic effect Effects 0.000 description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 5
239000008363 phosphate buffer Substances 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
235000009518 sodium iodide Nutrition 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000011877 solvent mixture Substances 0.000 description 5
238000005406 washing Methods 0.000 description 5
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 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical class P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
241000589517 Pseudomonas aeruginosa Species 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
WQQUFTSPNFODHK-SWLSCSKDSA-N s-[(2r,3s)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-oxoazetidin-2-yl] 5-(tetrazol-1-yl)pentanethioate Chemical compound N1C(=O)[C@H](CO[Si](C)(C)C(C)(C)C)[C@H]1SC(=O)CCCCN1N=NN=C1 WQQUFTSPNFODHK-SWLSCSKDSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical class [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
LHIQKOJFPKVRSX-PKKHVXKMSA-M sodium (5R,6S)-6-hydroxy-5-methyl-7-oxo-3-[4-(tetrazol-1-yl)butyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound N1(N=NN=C1)CCCCC=1S[C@]2(N(C=1C(=O)[O-])C([C@@H]2O)=O)C.[Na+] LHIQKOJFPKVRSX-PKKHVXKMSA-M 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
MIGIFQFSLQVLOA-VTNUGQMMSA-M sodium;(5r,6s)-6-(hydroxymethyl)-7-oxo-3-(tetrazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@H](C(N1C=1C([O-])=O)=O)CO)C=1CN1C=NN=N1 MIGIFQFSLQVLOA-VTNUGQMMSA-M 0.000 description 1
FFDDTLTWGMXRNK-XEDRIYAZSA-M sodium;(5r,6s)-6-(hydroxymethyl)-7-oxo-3-[2-(tetrazol-1-yl)ethyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@H](C(N1C=1C([O-])=O)=O)CO)C=1CCN1C=NN=N1 FFDDTLTWGMXRNK-XEDRIYAZSA-M 0.000 description 1
RGDLPFZTFFMVQT-VNYQHEISSA-M sodium;(5r,6s)-6-(hydroxymethyl)-7-oxo-3-[4-(tetrazol-1-yl)butyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@H](C(N1C=1C([O-])=O)=O)CO)C=1CCCCN1C=NN=N1 RGDLPFZTFFMVQT-VNYQHEISSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
239000013638 trimer Substances 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1