BE887428A - Antibiotiques a noyau beta-lactame, et procede pour les preparer - Google Patents

Info

Publication number

BE887428A

BE887428A BE0/203736A BE203736A BE887428A BE 887428 A BE887428 A BE 887428A BE 0/203736 A BE0/203736 A BE 0/203736A BE 203736 A BE203736 A BE 203736A BE 887428 A BE887428 A BE 887428A

Authority

BE

Belgium

Prior art keywords

emi

radical

group

amine

alkyl

Prior art date

1980-02-07

Links

• Espacenet
• Global Dossier
• Discuss

• 238000004519 manufacturing process Methods 0.000 title description 10
• 239000003242 anti bacterial agent Substances 0.000 title description 3
• 229940088710 antibiotic agent Drugs 0.000 title description 2
• 150000003952 β-lactams Chemical group 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 272
• 239000000203 mixture Substances 0.000 claims description 270
• -1 substituent sulfonic acid salt Chemical class 0.000 claims description 134
• 239000002253 acid Substances 0.000 claims description 113
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 109
• 238000000034 method Methods 0.000 claims description 80
• 229910052757 nitrogen Inorganic materials 0.000 claims description 60
• 150000003839 salts Chemical class 0.000 claims description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 54
• 239000000284 extract Substances 0.000 claims description 41
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
• 239000001257 hydrogen Substances 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 150000003254 radicals Chemical group 0.000 claims description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 244000005700 microbiome Species 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 150000001412 amines Chemical class 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 238000006277 sulfonation reaction Methods 0.000 claims description 16
• 125000003277 amino group Chemical group 0.000 claims description 15
• 150000001768 cations Chemical class 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 241000588879 Chromobacterium violaceum Species 0.000 claims description 14
• 125000006239 protecting group Chemical group 0.000 claims description 14
• 150000001408 amides Chemical class 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 12
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 11
• 241000589236 Gluconobacter Species 0.000 claims description 10
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 9
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
• 229920001817 Agar Polymers 0.000 claims description 8
• 239000008272 agar Substances 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
• 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 claims description 6
• IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical class [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 239000000460 chlorine Substances 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 239000008103 glucose Substances 0.000 claims description 6
• WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
• ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 229940041514 candida albicans extract Drugs 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229940067157 phenylhydrazine Drugs 0.000 claims description 5
• 238000007363 ring formation reaction Methods 0.000 claims description 5
• IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 5
• 239000012138 yeast extract Substances 0.000 claims description 5
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 238000002360 preparation method Methods 0.000 claims description 4
• 230000010933 acylation Effects 0.000 claims description 3
• 238000005917 acylation reaction Methods 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 claims description 2
• SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims 8
• VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical class CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 7
• WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 5
• HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
• 125000001931 aliphatic group Chemical group 0.000 claims 2
• 150000003973 alkyl amines Chemical class 0.000 claims 2
• 125000005907 alkyl ester group Chemical group 0.000 claims 2
• 125000000304 alkynyl group Chemical group 0.000 claims 2
• 239000012736 aqueous medium Substances 0.000 claims 2
• 235000015278 beef Nutrition 0.000 claims 2
• 125000004970 halomethyl group Chemical group 0.000 claims 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
• BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical compound ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 claims 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims 2
• 108090000623 proteins and genes Proteins 0.000 claims 2
• 125000005504 styryl group Chemical group 0.000 claims 2
• 239000011593 sulfur Substances 0.000 claims 2
• 229910052717 sulfur Inorganic materials 0.000 claims 2
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
• 125000004122 cyclic group Chemical group 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 239000002243 precursor Substances 0.000 claims 1
• 239000000376 reactant Substances 0.000 claims 1
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 553
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 442
• 239000000243 solution Substances 0.000 description 281
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 280
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 262
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 256
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 244
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 241
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 165
• 239000002904 solvent Substances 0.000 description 105
• 239000000047 product Substances 0.000 description 95
• 239000007787 solid Substances 0.000 description 92
• 238000002844 melting Methods 0.000 description 89
• 230000008018 melting Effects 0.000 description 89
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
• 238000003756 stirring Methods 0.000 description 74
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 74
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 62
• 238000004587 chromatography analysis Methods 0.000 description 60
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 59
• 238000000354 decomposition reaction Methods 0.000 description 58
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
• 239000000706 filtrate Substances 0.000 description 57
• 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 56
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 51
• 239000000725 suspension Substances 0.000 description 51
• 238000001914 filtration Methods 0.000 description 49
• 235000011152 sodium sulphate Nutrition 0.000 description 49
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 48
• 229910052938 sodium sulfate Inorganic materials 0.000 description 48
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 47
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 46
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 43
• SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 37
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• 235000019796 monopotassium phosphate Nutrition 0.000 description 36
• GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 36
• 239000000126 substance Substances 0.000 description 36
• 239000010410 layer Substances 0.000 description 35
• 229940111688 monobasic potassium phosphate Drugs 0.000 description 35
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
• 239000012043 crude product Substances 0.000 description 33
• 239000003480 eluent Substances 0.000 description 33
• 239000002244 precipitate Substances 0.000 description 33
• 239000011541 reaction mixture Substances 0.000 description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• 239000003054 catalyst Substances 0.000 description 32
• 239000011347 resin Substances 0.000 description 31
• 229920005989 resin Polymers 0.000 description 31
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
• 239000000741 silica gel Substances 0.000 description 30
• 229910002027 silica gel Inorganic materials 0.000 description 30
• 238000010828 elution Methods 0.000 description 29
• 238000006243 chemical reaction Methods 0.000 description 28
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 27
• 239000012044 organic layer Substances 0.000 description 26
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 25
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 25
• 239000003795 chemical substances by application Substances 0.000 description 24
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 23
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 23
• 238000000746 purification Methods 0.000 description 23
• 239000011780 sodium chloride Substances 0.000 description 23
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
• 239000002609 medium Substances 0.000 description 22
• 235000017557 sodium bicarbonate Nutrition 0.000 description 22
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 19
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
• 239000007864 aqueous solution Substances 0.000 description 18
• 239000012298 atmosphere Substances 0.000 description 18
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
• 239000003208 petroleum Substances 0.000 description 18
• 239000011591 potassium Substances 0.000 description 18
• 229910052700 potassium Inorganic materials 0.000 description 18
• 238000005406 washing Methods 0.000 description 18
• 239000004202 carbamide Substances 0.000 description 17
• 238000001816 cooling Methods 0.000 description 17
• 239000012452 mother liquor Substances 0.000 description 17
• 238000001665 trituration Methods 0.000 description 17
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
• 230000002829 reductive effect Effects 0.000 description 16
• 229910052786 argon Inorganic materials 0.000 description 15
• 238000001035 drying Methods 0.000 description 15
• 238000000855 fermentation Methods 0.000 description 14
• 230000004151 fermentation Effects 0.000 description 14
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 14
• 239000008057 potassium phosphate buffer Substances 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 13
• 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 13
• 229910000027 potassium carbonate Inorganic materials 0.000 description 13
• 235000011181 potassium carbonates Nutrition 0.000 description 13
• 229910052708 sodium Inorganic materials 0.000 description 13
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 238000002425 crystallisation Methods 0.000 description 12
• 230000008025 crystallization Effects 0.000 description 12
• 239000011734 sodium Substances 0.000 description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
• 238000010790 dilution Methods 0.000 description 11
• 239000012895 dilution Substances 0.000 description 11
• 238000001704 evaporation Methods 0.000 description 11
• 230000008020 evaporation Effects 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 238000001953 recrystallisation Methods 0.000 description 11
• 241000894007 species Species 0.000 description 11
• 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 10
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 10
• 230000003115 biocidal effect Effects 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 238000004108 freeze drying Methods 0.000 description 10
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
• 238000004440 column chromatography Methods 0.000 description 9
• 235000019253 formic acid Nutrition 0.000 description 9
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 7
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
• 239000000538 analytical sample Substances 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 239000013078 crystal Substances 0.000 description 7
• 239000003456 ion exchange resin Substances 0.000 description 7
• 229920003303 ion-exchange polymer Polymers 0.000 description 7
• 150000003222 pyridines Chemical class 0.000 description 7
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