CA1340253C - B-lactam antibiotics - Google Patents

Info

Publication number

CA1340253C

CA1340253C CA000617057A CA617057A CA1340253C CA 1340253 C CA1340253 C CA 1340253C CA 000617057 A CA000617057 A CA 000617057A CA 617057 A CA617057 A CA 617057A CA 1340253 C CA1340253 C CA 1340253C

Authority

CA

Canada

Prior art keywords

amino

oxo

acid

salt

beta

Prior art date

1980-02-07

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• CIPO
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• 239000003782 beta lactam antibiotic agent Substances 0.000 title description 5
• -1 2-phenylethenyl Chemical group 0.000 claims abstract description 297
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
• 125000002252 acyl group Chemical group 0.000 claims abstract description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
• 150000001768 cations Chemical class 0.000 claims abstract description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 9
• 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 5
• 229910006067 SO3−M Inorganic materials 0.000 claims abstract 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 367
• 239000002253 acid Substances 0.000 claims description 217
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 132
• 239000000203 mixture Substances 0.000 claims description 124
• 239000001257 hydrogen Substances 0.000 claims description 94
• 229910052739 hydrogen Inorganic materials 0.000 claims description 94
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
• 150000003839 salts Chemical class 0.000 claims description 82
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 80
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 150000002367 halogens Chemical group 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000003118 aryl group Chemical group 0.000 claims description 7
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
• 125000003368 amide group Chemical group 0.000 claims description 6
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
• 229910006069 SO3H Inorganic materials 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
• 125000004442 acylamino group Chemical group 0.000 claims description 3
• 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 3
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
• 125000001931 aliphatic group Chemical group 0.000 claims description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 12
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 5
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 5
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 5
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 5
• 230000000844 anti-bacterial effect Effects 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 125000003277 amino group Chemical group 0.000 abstract description 8
• 239000003242 anti bacterial agent Substances 0.000 abstract description 2
• 229910006127 SO3X Inorganic materials 0.000 abstract 1
• 229940088710 antibiotic agent Drugs 0.000 abstract 1
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 415
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 327
• 239000000243 solution Substances 0.000 description 245
• 150000001875 compounds Chemical class 0.000 description 240
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 217
• 229910001868 water Inorganic materials 0.000 description 205
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 198
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 191
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 186
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 185
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 171
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 153
• 238000002844 melting Methods 0.000 description 146
• 230000008018 melting Effects 0.000 description 146
• 239000000047 product Substances 0.000 description 93
• 235000013350 formula milk Nutrition 0.000 description 90
• 238000000034 method Methods 0.000 description 83
• 239000002904 solvent Substances 0.000 description 81
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 76
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 75
• 238000003756 stirring Methods 0.000 description 65
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 62
• 239000007787 solid Substances 0.000 description 62
• 239000003921 oil Substances 0.000 description 56
• 238000007792 addition Methods 0.000 description 52
• LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 48
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 45
• 239000000706 filtrate Substances 0.000 description 45
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 42
• 238000006243 chemical reaction Methods 0.000 description 41
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 40
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 38
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
• 229960003424 phenylacetic acid Drugs 0.000 description 36
• 239000002002 slurry Substances 0.000 description 32
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
• 229940111688 monobasic potassium phosphate Drugs 0.000 description 29
• 235000019796 monopotassium phosphate Nutrition 0.000 description 29
• GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 28
• 239000012043 crude product Substances 0.000 description 28
• 239000000284 extract Substances 0.000 description 28
• 229910052938 sodium sulfate Inorganic materials 0.000 description 28
• 235000011152 sodium sulphate Nutrition 0.000 description 28
• 238000004587 chromatography analysis Methods 0.000 description 27
• 238000010828 elution Methods 0.000 description 27
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 27
• 239000000741 silica gel Substances 0.000 description 27
• 229910002027 silica gel Inorganic materials 0.000 description 27
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 26
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
• 239000003795 chemical substances by application Substances 0.000 description 25
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 25
• 239000000463 material Substances 0.000 description 25
• 239000002244 precipitate Substances 0.000 description 25
• 238000001914 filtration Methods 0.000 description 23
• 239000003054 catalyst Substances 0.000 description 22
• 239000003480 eluent Substances 0.000 description 22
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
• 239000010410 layer Substances 0.000 description 21
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• 239000011347 resin Substances 0.000 description 20
• 229920005989 resin Polymers 0.000 description 20
• 239000012044 organic layer Substances 0.000 description 19
• 238000000746 purification Methods 0.000 description 19
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
• 244000005700 microbiome Species 0.000 description 18
• 229910052700 potassium Inorganic materials 0.000 description 18
• 239000011591 potassium Substances 0.000 description 18
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 17
• 238000004458 analytical method Methods 0.000 description 17
• 230000000875 corresponding effect Effects 0.000 description 17
• 238000001665 trituration Methods 0.000 description 17
• JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 16
• 239000012298 atmosphere Substances 0.000 description 16
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 16
• 239000002609 medium Substances 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 15
• 238000004108 freeze drying Methods 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
• 239000007864 aqueous solution Substances 0.000 description 14
• 239000004202 carbamide Substances 0.000 description 14
• 239000012452 mother liquor Substances 0.000 description 14
• DAKDZRFZKWOQEG-DKWTVANSSA-M potassium (3S)-3-amino-2-oxoazetidine-1-sulfonate Chemical compound N[C@@H]1C(N(C1)S(=O)(=O)[O-])=O.[K+] DAKDZRFZKWOQEG-DKWTVANSSA-M 0.000 description 14
• OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 14
• 125000006239 protecting group Chemical group 0.000 description 14
• 235000017557 sodium bicarbonate Nutrition 0.000 description 14
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
• KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 13
• 238000001035 drying Methods 0.000 description 13
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 13
• 239000008057 potassium phosphate buffer Substances 0.000 description 13
• 229920006395 saturated elastomer Polymers 0.000 description 13
• 229960001407 sodium bicarbonate Drugs 0.000 description 13
• 229940086542 triethylamine Drugs 0.000 description 13
• GDMSQJFJWOAAIG-WNQIDUERSA-M (3S)-3-amino-2-oxoazetidine-1-sulfonate tetrabutylazanium Chemical compound N[C@H]1CN(C1=O)S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC GDMSQJFJWOAAIG-WNQIDUERSA-M 0.000 description 12
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 12
• 241000588879 Chromobacterium violaceum Species 0.000 description 12
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
• 238000001704 evaporation Methods 0.000 description 12
• 230000008020 evaporation Effects 0.000 description 12
• 239000000543 intermediate Substances 0.000 description 12
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
• 239000011780 sodium chloride Substances 0.000 description 12
• 238000006277 sulfonation reaction Methods 0.000 description 12
• 238000005406 washing Methods 0.000 description 12
• 238000002425 crystallisation Methods 0.000 description 11
• 230000008025 crystallization Effects 0.000 description 11
• 235000011167 hydrochloric acid Nutrition 0.000 description 11
• 229960000443 hydrochloric acid Drugs 0.000 description 11
• 238000001953 recrystallisation Methods 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 241000589236 Gluconobacter Species 0.000 description 10
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• 235000011181 potassium carbonates Nutrition 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
• 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
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
• 229910052786 argon Inorganic materials 0.000 description 9
• 238000004440 column chromatography Methods 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
• 238000004519 manufacturing process Methods 0.000 description 9
• 150000003222 pyridines Chemical class 0.000 description 9
• 229910052708 sodium Inorganic materials 0.000 description 9
• ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 8
• FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 8
• YFNGMHWZSSKMAC-UHFFFAOYSA-M 3-amino-3-methoxy-2-oxoazetidine-1-sulfonate tetrabutylazanium Chemical compound COC1(N)CN(C1=O)S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC YFNGMHWZSSKMAC-UHFFFAOYSA-M 0.000 description 8
• 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 8
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• 239000008103 glucose Substances 0.000 description 8
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
• 229920001817 Agar Polymers 0.000 description 7
• 239000007868 Raney catalyst Substances 0.000 description 7
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 7
• 229910000564 Raney nickel Inorganic materials 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
• 239000008272 agar Substances 0.000 description 7
• 239000000538 analytical sample Substances 0.000 description 7
• 230000003115 biocidal effect Effects 0.000 description 7
• 229910021538 borax Inorganic materials 0.000 description 7
• 229940041514 candida albicans extract Drugs 0.000 description 7
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 7
• 238000010511 deprotection reaction Methods 0.000 description 7
• 238000010790 dilution Methods 0.000 description 7
• 239000012895 dilution Substances 0.000 description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
• 239000003960 organic solvent Substances 0.000 description 7
• 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
• 235000010339 sodium tetraborate Nutrition 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 239000012138 yeast extract Substances 0.000 description 7
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
• 239000007832 Na2SO4 Substances 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 229910052799 carbon Inorganic materials 0.000 description 6
• 238000005119 centrifugation Methods 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
• CDMADVZSLOHIFP-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane;decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 CDMADVZSLOHIFP-UHFFFAOYSA-N 0.000 description 6
• 238000000855 fermentation Methods 0.000 description 6
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• JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 6
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• TVHCXXXXQNWQLP-DMTCNVIQSA-N methyl (2s,3r)-2-amino-3-hydroxybutanoate Chemical compound COC(=O)[C@@H](N)[C@@H](C)O TVHCXXXXQNWQLP-DMTCNVIQSA-N 0.000 description 1
• XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
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• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
• FHFYAOSPDILBTL-SNVBAGLBSA-N n-[(3r)-3-methoxy-2-oxoazetidin-1-yl]-2-phenylacetamide Chemical compound O=C1[C@H](OC)CN1NC(=O)CC1=CC=CC=C1 FHFYAOSPDILBTL-SNVBAGLBSA-N 0.000 description 1
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• REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
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• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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• CETSHBMYUDCSRJ-UHFFFAOYSA-M potassium 3-amino-3-methoxy-2-oxoazetidine-1-sulfonate Chemical compound NC1(C(N(C1)S(=O)(=O)[O-])=O)OC.[K+] CETSHBMYUDCSRJ-UHFFFAOYSA-M 0.000 description 1
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• 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 1
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