IE51392B1

IE51392B1 - Beta-lactam antibiotics

Beta-lactam antibiotics

Info

Publication number: IE51392B1
Authority: IE; Ireland
Prior art keywords: amino; hydrogen; salt; oxo; accordance
Prior art date: 1980-02-07

Application number

IE230/81A

Other languages

English (en)

Other versions

IE810230L (en

Original Assignee

Squibb & Sons Inc

Priority date

1980-02-07

Filing date

1981-02-06

Publication date

1986-12-24

1981-02-06 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1981-02-06 Priority to IE2297/86A priority Critical patent/IE51393B1/en

1981-08-07 Publication of IE810230L publication Critical patent/IE810230L/xx

1986-12-24 Publication of IE51392B1 publication Critical patent/IE51392B1/en

Links

239000003782 beta lactam antibiotic agent Substances 0.000 title abstract description 5
239000002132 β-lactam antibiotic Substances 0.000 title abstract description 5
229940124586 β-lactam antibiotics Drugs 0.000 title abstract description 5
-1 2-phenylethenyl Chemical group 0.000 claims abstract description 310
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 268
150000001875 compounds Chemical class 0.000 claims abstract description 255
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 133
239000001257 hydrogen Substances 0.000 claims abstract description 132
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 60
125000000217 alkyl group Chemical group 0.000 claims abstract description 56
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
125000002252 acyl group Chemical group 0.000 claims abstract description 27
150000001768 cations Chemical class 0.000 claims abstract description 25
125000006239 protecting group Chemical group 0.000 claims abstract description 13
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
150000002431 hydrogen Chemical class 0.000 claims abstract 27
239000002253 acid Substances 0.000 claims description 233
239000000203 mixture Substances 0.000 claims description 122
238000000034 method Methods 0.000 claims description 115
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 98
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 97
125000001841 imino group Chemical group [H]N=* 0.000 claims description 78
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 74
150000003952 β-lactams Chemical class 0.000 claims description 69
150000003839 salts Chemical class 0.000 claims description 63
229910052757 nitrogen Inorganic materials 0.000 claims description 54
238000006243 chemical reaction Methods 0.000 claims description 42
125000003545 alkoxy group Chemical group 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 38
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 27
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
238000006277 sulfonation reaction Methods 0.000 claims description 15
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 12
230000002829 reductive effect Effects 0.000 claims description 12
125000000852 azido group Chemical class *N=[N+]=[N-] 0.000 claims description 11
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 claims description 11
125000004434 sulfur atom Chemical group 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical group OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 claims description 10
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 10
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000003368 amide group Chemical group 0.000 claims description 9
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 7
AFDQGRURHDVABZ-UHFFFAOYSA-N n,n-dimethylformamide;sulfur trioxide Chemical group O=S(=O)=O.CN(C)C=O AFDQGRURHDVABZ-UHFFFAOYSA-N 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
238000007363 ring formation reaction Methods 0.000 claims description 6
150000003460 sulfonic acids Chemical class 0.000 claims description 6
238000005917 acylation reaction Methods 0.000 claims description 5
125000005276 alkyl hydrazino group Chemical group 0.000 claims description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
208000035143 Bacterial infection Diseases 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
208000022362 bacterial infectious disease Diseases 0.000 claims description 3
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
229910001414 potassium ion Inorganic materials 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 9
125000005843 halogen group Chemical group 0.000 claims 6
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 4
125000001931 aliphatic group Chemical group 0.000 claims 2
125000005907 alkyl ester group Chemical group 0.000 claims 2
125000000304 alkynyl group Chemical group 0.000 claims 2
150000001540 azides Chemical class 0.000 claims 2
125000004970 halomethyl group Chemical class 0.000 claims 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
125000005504 styryl group Chemical group 0.000 claims 2
WGMACXZGDYGGGV-UHFFFAOYSA-N 2-methyl-4-oxoazetidine-1-sulfonic acid Chemical compound CC1CC(=O)N1S(O)(=O)=O WGMACXZGDYGGGV-UHFFFAOYSA-N 0.000 claims 1
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims 1
101100364844 Salinispora tropica (strain ATCC BAA-916 / DSM 44818 / CNB-440) salL gene Proteins 0.000 claims 1
239000003937 drug carrier Chemical group 0.000 claims 1
239000002243 precursor Substances 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 417
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 339
239000000243 solution Substances 0.000 description 251
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 246
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 211
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 197
229910001868 water Inorganic materials 0.000 description 196
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 186
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 175
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 159
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 114
238000002844 melting Methods 0.000 description 107
230000008018 melting Effects 0.000 description 107
239000000047 product Substances 0.000 description 92
239000002904 solvent Substances 0.000 description 81
238000003756 stirring Methods 0.000 description 66
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 47
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 45
239000000706 filtrate Substances 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
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
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-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
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 35
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
229940111688 monobasic potassium phosphate Drugs 0.000 description 33
235000019796 monopotassium phosphate Nutrition 0.000 description 33
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
239000002002 slurry Substances 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
229910052938 sodium sulfate Inorganic materials 0.000 description 29
235000011152 sodium sulphate Nutrition 0.000 description 29
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
238000004587 chromatography analysis Methods 0.000 description 28
239000012043 crude product Substances 0.000 description 28
239000000284 extract Substances 0.000 description 28
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 28
239000002244 precipitate Substances 0.000 description 28
238000010828 elution Methods 0.000 description 27
239000000741 silica gel Substances 0.000 description 27
229910002027 silica gel Inorganic materials 0.000 description 27
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 26
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
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
239000000463 material Substances 0.000 description 25
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 24
238000001914 filtration Methods 0.000 description 24
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
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
239000010410 layer Substances 0.000 description 20
244000005700 microbiome Species 0.000 description 20
239000012044 organic layer Substances 0.000 description 20
238000005481 NMR spectroscopy Methods 0.000 description 19
238000004458 analytical method Methods 0.000 description 19
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 19
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 19
239000011347 resin Substances 0.000 description 19
229920005989 resin Polymers 0.000 description 19
229920001467 poly(styrenesulfonates) Polymers 0.000 description 18
238000000746 purification Methods 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
239000002609 medium Substances 0.000 description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
KHUNFTAJVUPPCY-UHFFFAOYSA-N azetidine-1-sulfonic acid Chemical compound OS(=O)(=O)N1CCC1 KHUNFTAJVUPPCY-UHFFFAOYSA-N 0.000 description 14
238000004108 freeze drying Methods 0.000 description 14
239000012452 mother liquor Substances 0.000 description 14
229960003424 phenylacetic acid Drugs 0.000 description 14
239000008057 potassium phosphate buffer Substances 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
239000004202 carbamide Substances 0.000 description 13
238000001035 drying Methods 0.000 description 13
238000001704 evaporation Methods 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
238000005406 washing Methods 0.000 description 13
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
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 12
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 12
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
239000000725 suspension Substances 0.000 description 12
NSRVGDULUQOEBX-REOHCLBHSA-N (3s)-3-amino-2-oxoazetidine-1-sulfonic acid Chemical compound N[C@H]1CN(S(O)(=O)=O)C1=O NSRVGDULUQOEBX-REOHCLBHSA-N 0.000 description 11
238000002425 crystallisation Methods 0.000 description 11
230000008025 crystallization Effects 0.000 description 11
239000011780 sodium chloride Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
229910052786 argon Inorganic materials 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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
230000003115 biocidal effect Effects 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
238000001816 cooling Methods 0.000 description 9
150000003222 pyridines Chemical class 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 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
241000589236 Gluconobacter Species 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
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 8
235000019253 formic acid Nutrition 0.000 description 8
239000008103 glucose Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
229920001817 Agar Polymers 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
239000008272 agar Substances 0.000 description 7
239000000538 analytical sample Substances 0.000 description 7
229910021538 borax Inorganic materials 0.000 description 7
238000010790 dilution Methods 0.000 description 7
239000012895 dilution Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
235000010339 sodium tetraborate Nutrition 0.000 description 7
239000007858 starting material Substances 0.000 description 7
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 7
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 6
NONZZMVLNASYPE-UHFFFAOYSA-N 3-amino-3-methoxy-2-oxoazetidine-1-sulfonic acid Chemical compound COC1(N)CN(S(O)(=O)=O)C1=O NONZZMVLNASYPE-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
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 description 1
229950003332 perflubutane Drugs 0.000 description 1
238000007747 plating Methods 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000011176 pooling Methods 0.000 description 1
150000003109 potassium Chemical class 0.000 description 1
VDZHXBLLTKHLJR-UHFFFAOYSA-M potassium 3-butoxy-2-oxo-3-[(2-phenylacetyl)amino]azetidine-1-sulfonate Chemical compound C(CCC)OC1(C(N(C1)S(=O)(=O)[O-])=O)NC(CC1=CC=CC=C1)=O.[K+] VDZHXBLLTKHLJR-UHFFFAOYSA-M 0.000 description 1
ZOTJWAKJOOOXBM-UHFFFAOYSA-M potassium 3-methoxy-2-oxo-3-[(3-oxo-2-phenyl-3-phenylmethoxypropanoyl)amino]azetidine-1-sulfonate Chemical compound O=C(C(C(OCC1=CC=CC=C1)=O)C1=CC=CC=C1)NC1(C(N(C1)S(=O)(=O)[O-])=O)OC.[K+] ZOTJWAKJOOOXBM-UHFFFAOYSA-M 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LJCNRYVRMXRIQR-UHFFFAOYSA-L potassium sodium tartrate Chemical compound [Na+].[K+].[O-]C(=O)C(O)C(O)C([O-])=O LJCNRYVRMXRIQR-UHFFFAOYSA-L 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
229940080818 propionamide Drugs 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
238000005245 sintering Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
PIQQONBHNFGELI-UHFFFAOYSA-N tert-butyl n-(1-methoxy-2-methyl-4-oxoazetidin-3-yl)carbamate Chemical compound CON1C(C)C(NC(=O)OC(C)(C)C)C1=O PIQQONBHNFGELI-UHFFFAOYSA-N 0.000 description 1
BNHJMVYSNXQXKI-WDSKDSINSA-N tert-butyl n-[(2s,3s)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate Chemical compound C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N1O BNHJMVYSNXQXKI-WDSKDSINSA-N 0.000 description 1
XSYFPNDNVLNEMI-BQBZGAKWSA-N tert-butyl n-[(2s,3s)-2-ethyl-4-oxoazetidin-3-yl]carbamate Chemical compound CC[C@@H]1NC(=O)[C@H]1NC(=O)OC(C)(C)C XSYFPNDNVLNEMI-BQBZGAKWSA-N 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
DZXKSFDSPBRJPS-UHFFFAOYSA-N tin(2+);sulfide Chemical compound [S-2].[Sn+2] DZXKSFDSPBRJPS-UHFFFAOYSA-N 0.000 description 1
NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000005051 trimethylchlorosilane Substances 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
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
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
239000006150 trypticase soy agar Substances 0.000 description 1
229960004799 tryptophan Drugs 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1