DD142342A5 - Verfahren zur herstellung von 6-substituierten thiaazaverbindungen - Google Patents

Info

Publication number

DD142342A5

DD142342A5 DD79210799A DD21079979A DD142342A5 DD 142342 A5 DD142342 A5 DD 142342A5 DD 79210799 A DD79210799 A DD 79210799A DD 21079979 A DD21079979 A DD 21079979A DD 142342 A5 DD142342 A5 DD 142342A5

Authority

DD

German Democratic Republic

Prior art keywords

lower alkyl

substituted

hydroxy

amino

alkyl

Prior art date

1978-02-02

Links

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• 238000000034 method Methods 0.000 title claims abstract description 48
• 238000004519 manufacturing process Methods 0.000 title claims 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 340
• 150000003839 salts Chemical class 0.000 claims abstract description 70
• 238000002360 preparation method Methods 0.000 claims abstract description 16
• -1 hydroxy, mercapto Chemical group 0.000 claims description 702
• 125000000217 alkyl group Chemical group 0.000 claims description 237
• 239000000203 mixture Substances 0.000 claims description 104
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 92
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 91
• 125000004432 carbon atom Chemical group C* 0.000 claims description 90
• 125000003545 alkoxy group Chemical group 0.000 claims description 72
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 68
• 125000004423 acyloxy group Chemical group 0.000 claims description 63
• 229910052757 nitrogen Inorganic materials 0.000 claims description 63
• 229910052736 halogen Inorganic materials 0.000 claims description 62
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
• 150000002367 halogens Chemical class 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 46
• 125000002252 acyl group Chemical group 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 125000004414 alkyl thio group Chemical group 0.000 claims description 33
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 29
• 150000002148 esters Chemical class 0.000 claims description 26
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 26
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
• 125000001931 aliphatic group Chemical group 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
• 239000004215 Carbon black (E152) Substances 0.000 claims description 19
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 19
• 229930195733 hydrocarbon Natural products 0.000 claims description 19
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 125000005108 alkenylthio group Chemical group 0.000 claims description 16
• 125000001544 thienyl group Chemical group 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 12
• 125000003277 amino group Chemical group 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
• 239000012442 inert solvent Substances 0.000 claims description 11
• 230000007935 neutral effect Effects 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000524 functional group Chemical group 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 230000004962 physiological condition Effects 0.000 claims description 7
• 238000010438 heat treatment Methods 0.000 claims description 6
• OWDWVSMHHYHKDJ-OMNKOJBGSA-N (5r)-3-(2-acetamidoethylsulfanyl)-6-ethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)C(CC)[C@H]21 OWDWVSMHHYHKDJ-OMNKOJBGSA-N 0.000 claims description 4
• 150000001768 cations Chemical class 0.000 claims description 4
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
• 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
• MEQOGUDGTVJOFC-VZVJOWETSA-N (5r)-3,6-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(C)=C(C(O)=O)N2C(=O)C(C)[C@H]21 MEQOGUDGTVJOFC-VZVJOWETSA-N 0.000 claims description 3
• PPTLBCAONHFKKQ-PHUNFMHTSA-N (5r)-3-(3-aminopropyl)-6-ethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(CCCN)=C(C(O)=O)N2C(=O)C(CC)[C@H]21 PPTLBCAONHFKKQ-PHUNFMHTSA-N 0.000 claims description 3
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• UCSQQBWLTSTJJW-IOJJLOCKSA-N (5r)-3-ethylsulfanyl-7-oxo-6-propan-2-yl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(SCC)=C(C(O)=O)N2C(=O)C(C(C)C)[C@@H]12 UCSQQBWLTSTJJW-IOJJLOCKSA-N 0.000 claims description 2
• DUNKKIRUWZSMPT-RXMQYKEDSA-N (5r)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CS[C@@H]2CC(=O)N12 DUNKKIRUWZSMPT-RXMQYKEDSA-N 0.000 claims description 2
• 125000005496 phosphonium group Chemical group 0.000 claims 2
• QGJRORLEGKFOCP-IONNQARKSA-N (5r,6s)-3-(3-aminopropyl)-6-methoxy-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(CCCN)=C(C(O)=O)N2C(=O)[C@H](OC)[C@H]21 QGJRORLEGKFOCP-IONNQARKSA-N 0.000 claims 1
• PMMXECSIWSQAEG-GXTWGEPZSA-N (5r,6s)-3-methyl-7-oxo-6-(2-phenoxyacetyl)oxy-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound O([C@@H]1[C@@H]2N(C1=O)C(=C(S2)C)C(O)=O)C(=O)COC1=CC=CC=C1 PMMXECSIWSQAEG-GXTWGEPZSA-N 0.000 claims 1
• RHMQSFFWLGIABS-CAHLUQPWSA-N (5r,6s)-6-methoxy-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(C)=C(C(O)=O)N2C(=O)[C@H](OC)[C@H]21 RHMQSFFWLGIABS-CAHLUQPWSA-N 0.000 claims 1
• 125000005233 alkylalcohol group Chemical group 0.000 claims 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
• 125000005309 thioalkoxy group Chemical group 0.000 claims 1
• 239000003242 anti bacterial agent Substances 0.000 abstract 1
• 229940088710 antibiotic agent Drugs 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 333
• 239000000243 solution Substances 0.000 description 171
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 150
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 92
• 238000002329 infrared spectrum Methods 0.000 description 90
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 84
• 238000010521 absorption reaction Methods 0.000 description 83
• OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 81
• 239000000741 silica gel Substances 0.000 description 73
• 229910002027 silica gel Inorganic materials 0.000 description 73
• 150000003254 radicals Chemical class 0.000 description 69
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
• 239000000460 chlorine Substances 0.000 description 65
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 58
• 238000006243 chemical reaction Methods 0.000 description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 48
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 46
• 239000002253 acid Substances 0.000 description 45
• 229910052938 sodium sulfate Inorganic materials 0.000 description 45
• 235000011152 sodium sulphate Nutrition 0.000 description 45
• 238000004809 thin layer chromatography Methods 0.000 description 45
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
• 239000002904 solvent Substances 0.000 description 43
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• 239000002585 base Substances 0.000 description 36
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 32
• 238000004587 chromatography analysis Methods 0.000 description 30
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
• 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 30
• 235000017557 sodium bicarbonate Nutrition 0.000 description 29
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 29
• 229910052801 chlorine Inorganic materials 0.000 description 28
• 239000012074 organic phase Substances 0.000 description 28
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 27
• 239000007858 starting material Substances 0.000 description 26
• 239000000706 filtrate Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000003795 chemical substances by application Substances 0.000 description 24
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
• 239000003054 catalyst Substances 0.000 description 23
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• 239000002808 molecular sieve Substances 0.000 description 22
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 22
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 19
• 229910052783 alkali metal Inorganic materials 0.000 description 19
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
• 150000001340 alkali metals Chemical class 0.000 description 16
• 125000004043 oxo group Chemical group O=* 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
• 238000006722 reduction reaction Methods 0.000 description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
• 229910052794 bromium Inorganic materials 0.000 description 14
• 125000001309 chloro group Chemical group Cl* 0.000 description 14
• BGUUGGZDHDSUBB-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-ethoxy-2-hydroxyacetate Chemical compound CCOC(O)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 BGUUGGZDHDSUBB-UHFFFAOYSA-N 0.000 description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 150000007513 acids Chemical class 0.000 description 13
• 150000001721 carbon Chemical group 0.000 description 13
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 13
• 125000005843 halogen group Chemical group 0.000 description 13
• 239000000543 intermediate Substances 0.000 description 13
• 239000007788 liquid Substances 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 12
• 239000008346 aqueous phase Substances 0.000 description 12
• 230000003197 catalytic effect Effects 0.000 description 12
• 125000000753 cycloalkyl group Chemical group 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
• 238000005406 washing Methods 0.000 description 12
• 239000003638 chemical reducing agent Substances 0.000 description 11
• 238000002425 crystallisation Methods 0.000 description 11
• 230000008025 crystallization Effects 0.000 description 11
• 238000002844 melting Methods 0.000 description 11
• 230000008018 melting Effects 0.000 description 11
• 229910052751 metal Inorganic materials 0.000 description 11
• 239000002184 metal Substances 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
• 238000000926 separation method Methods 0.000 description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• 229930182555 Penicillin Natural products 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 10
• 239000011737 fluorine Substances 0.000 description 10
• 229910052731 fluorine Inorganic materials 0.000 description 10
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 10
• 239000012299 nitrogen atmosphere Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 239000011734 sodium Substances 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 9
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 9
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 9
• 238000005984 hydrogenation reaction Methods 0.000 description 9
• 125000002950 monocyclic group Chemical group 0.000 description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 239000011701 zinc Substances 0.000 description 9
• 229910052725 zinc Inorganic materials 0.000 description 9
• 239000005909 Kieselgur Substances 0.000 description 8
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
• 229960000583 acetic acid Drugs 0.000 description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
• 230000002378 acidificating effect Effects 0.000 description 8
• 239000012267 brine Substances 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 8
• 229940049954 penicillin Drugs 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• 235000011121 sodium hydroxide Nutrition 0.000 description 8
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 8
• DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 7
• 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 7
• 150000003973 alkyl amines Chemical class 0.000 description 7
• 125000002947 alkylene group Chemical group 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 238000003776 cleavage reaction Methods 0.000 description 7
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 7
• 230000000269 nucleophilic effect Effects 0.000 description 7
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• 230000007017 scission Effects 0.000 description 7
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 7
• YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 6
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• 229930195725 Mannitol Natural products 0.000 description 6
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• 150000003952 β-lactams Chemical group 0.000 description 1