DD144779A5 - Verfahren zur herstellung von 7 beta-aminothiazolyl-acetamido-3-cephem-4-carbonsaeure-verbindungen - Google Patents

Info

Publication number

DD144779A5

DD144779A5 DD79214148A DD21414879A DD144779A5 DD 144779 A5 DD144779 A5 DD 144779A5 DD 79214148 A DD79214148 A DD 79214148A DD 21414879 A DD21414879 A DD 21414879A DD 144779 A5 DD144779 A5 DD 144779A5

Authority

DD

German Democratic Republic

Prior art keywords

formula

group

amino

compound

cephem

Prior art date

1978-07-07

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 47
• 238000002360 preparation method Methods 0.000 title claims description 21
• 150000001875 compounds Chemical class 0.000 claims abstract description 116
• -1 amino, hydroxy Chemical group 0.000 claims description 287
• 239000002253 acid Substances 0.000 claims description 82
• 150000003839 salts Chemical class 0.000 claims description 67
• 239000001257 hydrogen Substances 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
• 239000007858 starting material Substances 0.000 claims description 48
• 239000003795 chemical substances by application Substances 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000000524 functional group Chemical group 0.000 claims description 24
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 22
• 125000003277 amino group Chemical group 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical group 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 16
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
• 229910052740 iodine Inorganic materials 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 9
• 229930195733 hydrocarbon Natural products 0.000 claims description 9
• 230000004962 physiological condition Effects 0.000 claims description 7
• 239000004215 Carbon black (E152) Substances 0.000 claims description 6
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
• 150000001782 cephems Chemical group 0.000 claims description 5
• 125000005633 phthalidyl group Chemical group 0.000 claims description 4
• 102100040141 Aminopeptidase O Human genes 0.000 claims description 3
• 108050008333 Aminopeptidase O Proteins 0.000 claims description 3
• AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 3
• 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims 6
• IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
• 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 1
• WAVQOKDKPHYRDY-GOSISDBHSA-N benzhydryl (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C([C@H]1SCC=2)C(=O)N1C=2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 WAVQOKDKPHYRDY-GOSISDBHSA-N 0.000 claims 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
• RRHDIMPYWXJQEC-UHFFFAOYSA-N n-(2-amino-1,3-thiazol-4-yl)acetamide Chemical compound CC(=O)NC1=CSC(N)=N1 RRHDIMPYWXJQEC-UHFFFAOYSA-N 0.000 claims 1
• 230000003115 biocidal effect Effects 0.000 abstract description 4
• 208000015181 infectious disease Diseases 0.000 abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 140
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
• 239000000243 solution Substances 0.000 description 75
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 34
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• 239000000203 mixture Substances 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
• 229910052757 nitrogen Inorganic materials 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
• 239000002585 base Substances 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 27
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
• 125000001931 aliphatic group Chemical group 0.000 description 25
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
• 150000003254 radicals Chemical class 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• 238000001816 cooling Methods 0.000 description 21
• 239000008186 active pharmaceutical agent Substances 0.000 description 20
• 125000003118 aryl group Chemical group 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 20
• 150000002148 esters Chemical class 0.000 description 20
• 229910052751 metal Inorganic materials 0.000 description 20
• 229960000583 acetic acid Drugs 0.000 description 19
• 239000002184 metal Substances 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 150000008064 anhydrides Chemical class 0.000 description 18
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
• 229910052783 alkali metal Inorganic materials 0.000 description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
• 229920006395 saturated elastomer Polymers 0.000 description 17
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 17
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
• 150000007513 acids Chemical class 0.000 description 16
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
• 239000003054 catalyst Substances 0.000 description 16
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
• 150000001340 alkali metals Chemical class 0.000 description 15
• 239000000741 silica gel Substances 0.000 description 15
• 229910002027 silica gel Inorganic materials 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
• 238000010521 absorption reaction Methods 0.000 description 14
• 239000003638 chemical reducing agent Substances 0.000 description 14
• 238000002329 infrared spectrum Methods 0.000 description 14
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 13
• 229910052801 chlorine Inorganic materials 0.000 description 13
• 238000010438 heat treatment Methods 0.000 description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
• 239000011541 reaction mixture Substances 0.000 description 13
• 238000006722 reduction reaction Methods 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 12
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
• 239000011780 sodium chloride Substances 0.000 description 12
• 159000000000 sodium salts Chemical class 0.000 description 12
• 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 11
• 125000003545 alkoxy group Chemical group 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 11
• 239000011261 inert gas Substances 0.000 description 11
• 239000012442 inert solvent Substances 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 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 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
• 235000011054 acetic acid Nutrition 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 238000007254 oxidation reaction Methods 0.000 description 10
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
• 238000000354 decomposition reaction Methods 0.000 description 9
• 239000012362 glacial acetic acid Substances 0.000 description 9
• 150000004820 halides Chemical class 0.000 description 9
• 150000008282 halocarbons Chemical class 0.000 description 9
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
• 150000007522 mineralic acids Chemical class 0.000 description 9
• 230000003647 oxidation Effects 0.000 description 9
• 238000002211 ultraviolet spectrum Methods 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
• 230000002378 acidificating effect Effects 0.000 description 8
• 150000003973 alkyl amines Chemical class 0.000 description 8
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• 230000007062 hydrolysis Effects 0.000 description 8
• 238000006460 hydrolysis reaction Methods 0.000 description 8
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
• 229910052698 phosphorus Inorganic materials 0.000 description 8
• 239000011574 phosphorus Substances 0.000 description 8
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 description 7
• 150000001735 carboxylic acids Chemical class 0.000 description 7
• 150000002170 ethers Chemical class 0.000 description 7
• 150000002576 ketones Chemical class 0.000 description 7
• 229910052744 lithium Inorganic materials 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 230000008018 melting Effects 0.000 description 7
• 150000002825 nitriles Chemical class 0.000 description 7
• 239000007800 oxidant agent Substances 0.000 description 7
• 230000002829 reductive effect Effects 0.000 description 7
• 229910052708 sodium Inorganic materials 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 238000003797 solvolysis reaction Methods 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
• 229910052725 zinc Inorganic materials 0.000 description 7
• 239000011701 zinc Substances 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-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
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
• 229930195725 Mannitol Natural products 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• 238000006136 alcoholysis reaction Methods 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 238000007327 hydrogenolysis reaction Methods 0.000 description 6
• 239000000594 mannitol Substances 0.000 description 6
• 235000010355 mannitol Nutrition 0.000 description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 235000011121 sodium hydroxide Nutrition 0.000 description 6
• 235000009518 sodium iodide Nutrition 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
• SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 5
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
• 239000004793 Polystyrene Substances 0.000 description 5
• 229920002472 Starch Polymers 0.000 description 5
• 230000003213 activating effect Effects 0.000 description 5
• 230000010933 acylation Effects 0.000 description 5
• 238000005917 acylation reaction Methods 0.000 description 5
• 150000003863 ammonium salts Chemical class 0.000 description 5
• 150000001805 chlorine compounds Chemical class 0.000 description 5
• 238000003776 cleavage reaction Methods 0.000 description 5
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• 238000005886 esterification reaction Methods 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 150000002500 ions Chemical class 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 235000019359 magnesium stearate Nutrition 0.000 description 5
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
• 230000000269 nucleophilic effect Effects 0.000 description 5
• 150000007530 organic bases Chemical class 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
• 150000003003 phosphines Chemical class 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 230000007017 scission Effects 0.000 description 5
• 229910052717 sulfur Inorganic materials 0.000 description 5
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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