CA1286661C - 2,6-disubstituted penem compounds - Google Patents

Info

Publication number

CA1286661C

CA1286661C CA000342069A CA342069A CA1286661C CA 1286661 C CA1286661 C CA 1286661C CA 000342069 A CA000342069 A CA 000342069A CA 342069 A CA342069 A CA 342069A CA 1286661 C CA1286661 C CA 1286661C

Authority

CA

Canada

Prior art keywords

ethyl

solution

mmol

ether

penem

Prior art date

1978-12-18

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

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• 150000002961 penems Chemical class 0.000 title abstract description 12
• 150000001875 compounds Chemical class 0.000 claims abstract description 167
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 78
• 239000001257 hydrogen Substances 0.000 claims abstract description 45
• 238000002360 preparation method Methods 0.000 claims abstract description 45
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
• 125000004185 ester group Chemical group 0.000 claims abstract description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 122
• 238000000034 method Methods 0.000 claims description 112
• 239000002904 solvent Substances 0.000 claims description 58
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
• 238000010992 reflux Methods 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 239000012039 electrophile Substances 0.000 claims description 16
• 150000002431 hydrogen Chemical group 0.000 claims description 9
• 239000003960 organic solvent Substances 0.000 claims description 8
• 239000012442 inert solvent Substances 0.000 claims description 6
• 125000006239 protecting group Chemical group 0.000 claims description 4
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 2
• 125000001424 substituent group Chemical group 0.000 abstract description 26
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 25
• 239000000543 intermediate Substances 0.000 abstract description 18
• 239000003795 chemical substances by application Substances 0.000 abstract description 12
• 230000003389 potentiating effect Effects 0.000 abstract description 4
• 239000003242 anti bacterial agent Substances 0.000 abstract description 3
• 125000001475 halogen functional group Chemical group 0.000 abstract 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 426
• 239000000243 solution Substances 0.000 description 333
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 264
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 229
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 220
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 216
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 214
• 239000000203 mixture Substances 0.000 description 212
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 194
• 229910001868 water Inorganic materials 0.000 description 193
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 192
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 137
• -1 carboxy, carboxy Chemical group 0.000 description 130
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 95
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 90
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 89
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 88
• 239000012267 brine Substances 0.000 description 87
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 86
• 239000007787 solid Substances 0.000 description 86
• 235000019439 ethyl acetate Nutrition 0.000 description 74
• 239000003921 oil Substances 0.000 description 72
• 235000019198 oils Nutrition 0.000 description 72
• 229940093499 ethyl acetate Drugs 0.000 description 66
• 239000011541 reaction mixture Substances 0.000 description 65
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 64
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 63
• 239000000741 silica gel Substances 0.000 description 62
• 229910002027 silica gel Inorganic materials 0.000 description 62
• 229960001866 silicon dioxide Drugs 0.000 description 62
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 61
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 57
• GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical group C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 57
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 57
• 239000000047 product Substances 0.000 description 51
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 51
• 150000002148 esters Chemical group 0.000 description 50
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 49
• 239000011734 sodium Substances 0.000 description 49
• 238000006243 chemical reaction Methods 0.000 description 48
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 46
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 46
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 44
• 239000002253 acid Substances 0.000 description 44
• 235000017557 sodium bicarbonate Nutrition 0.000 description 42
• 239000000460 chlorine Substances 0.000 description 40
• 238000001704 evaporation Methods 0.000 description 40
• 230000008020 evaporation Effects 0.000 description 40
• 239000000706 filtrate Substances 0.000 description 40
• 229910052709 silver Inorganic materials 0.000 description 40
• 239000004332 silver Substances 0.000 description 40
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 40
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 37
• 125000003118 aryl group Chemical group 0.000 description 37
• 238000003756 stirring Methods 0.000 description 37
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
• 125000000623 heterocyclic group Chemical class 0.000 description 33
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
• 239000002585 base Substances 0.000 description 31
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 31
• 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 30
• 125000003282 alkyl amino group Chemical group 0.000 description 30
• 235000019341 magnesium sulphate Nutrition 0.000 description 30
• 238000001914 filtration Methods 0.000 description 29
• 229910052708 sodium Inorganic materials 0.000 description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
• 239000007858 starting material Substances 0.000 description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
• 229960000443 hydrochloric acid Drugs 0.000 description 25
• 229960001407 sodium bicarbonate Drugs 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 235000011167 hydrochloric acid Nutrition 0.000 description 24
• 239000010410 layer Substances 0.000 description 24
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 23
• 229940086542 triethylamine Drugs 0.000 description 22
• 239000000284 extract Substances 0.000 description 21
• HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 21
• 238000000746 purification Methods 0.000 description 21
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 20
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
• 125000003545 alkoxy group Chemical group 0.000 description 20
• 239000003054 catalyst Substances 0.000 description 20
• 238000004587 chromatography analysis Methods 0.000 description 20
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• 229940043279 diisopropylamine Drugs 0.000 description 19
• 239000012299 nitrogen atmosphere Substances 0.000 description 19
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 18
• 238000005481 NMR spectroscopy Methods 0.000 description 18
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 18
• 239000003610 charcoal Substances 0.000 description 18
• 239000012074 organic phase Substances 0.000 description 18
• 229910052763 palladium Inorganic materials 0.000 description 18
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 17
• 229910052938 sodium sulfate Inorganic materials 0.000 description 17
• 235000011152 sodium sulphate Nutrition 0.000 description 17
• 125000001931 aliphatic group Chemical group 0.000 description 16
• WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 16
• 229910052757 nitrogen Inorganic materials 0.000 description 16
• 238000000935 solvent evaporation Methods 0.000 description 16
• 239000006188 syrup Substances 0.000 description 16
• 235000020357 syrup Nutrition 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 239000012346 acetyl chloride Substances 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 14
• 238000001816 cooling Methods 0.000 description 14
• 125000005843 halogen group Chemical group 0.000 description 14
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 14
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
• 239000002244 precipitate Substances 0.000 description 14
• 229910001961 silver nitrate Inorganic materials 0.000 description 14
• ZCTHWZKWCUEIHN-UHFFFAOYSA-N 4-tritylsulfanylazetidin-2-one Chemical compound N1C(=O)CC1SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZCTHWZKWCUEIHN-UHFFFAOYSA-N 0.000 description 13
• 229910052799 carbon Inorganic materials 0.000 description 13
• 239000003480 eluent Substances 0.000 description 13
• 239000006260 foam Substances 0.000 description 13
• 229910052760 oxygen Inorganic materials 0.000 description 13
• 238000005406 washing Methods 0.000 description 13
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 12
• WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 12
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 12
• 238000001035 drying Methods 0.000 description 12
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
• 239000002808 molecular sieve Substances 0.000 description 12
• 239000000377 silicon dioxide Substances 0.000 description 12
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000007832 Na2SO4 Substances 0.000 description 11
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• 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 10
• 239000008346 aqueous phase Substances 0.000 description 10
• 229910052681 coesite Inorganic materials 0.000 description 10
• 229910052906 cristobalite Inorganic materials 0.000 description 10
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 10
• 235000012239 silicon dioxide Nutrition 0.000 description 10
• 229910052682 stishovite Inorganic materials 0.000 description 10
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
• 229910052905 tridymite Inorganic materials 0.000 description 10
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 9
• 230000010933 acylation Effects 0.000 description 9
• 238000005917 acylation reaction Methods 0.000 description 9
• 150000001412 amines Chemical class 0.000 description 9
• 235000019270 ammonium chloride Nutrition 0.000 description 9
• 150000001450 anions Chemical class 0.000 description 9
• 238000002425 crystallisation Methods 0.000 description 9
• 230000008025 crystallization Effects 0.000 description 9
• 238000010348 incorporation Methods 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• HVRMNEPIBIGCNZ-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-oxoacetate Chemical compound [O-][N+](=O)C1=CC=C(COC(=O)C=O)C=C1 HVRMNEPIBIGCNZ-UHFFFAOYSA-N 0.000 description 8
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
• 125000005236 alkanoylamino group Chemical group 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 125000004414 alkyl thio group Chemical group 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 7
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 229910052700 potassium Inorganic materials 0.000 description 7
• 239000011591 potassium Substances 0.000 description 7
• 159000000000 sodium salts Chemical class 0.000 description 7
• DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 6
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 6
• HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 6
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• 125000004423 acyloxy group Chemical group 0.000 description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
• 125000001309 chloro group Chemical group Cl* 0.000 description 6
• 238000010828 elution Methods 0.000 description 6
• SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 6
• 229910000037 hydrogen sulfide Inorganic materials 0.000 description 6
• 238000005984 hydrogenation reaction Methods 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 238000011282 treatment Methods 0.000 description 6
• 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 6
• OEYMQQDJCUHKQS-UHFFFAOYSA-N (4-oxoazetidin-2-yl) acetate Chemical class CC(=O)OC1CC(=O)N1 OEYMQQDJCUHKQS-UHFFFAOYSA-N 0.000 description 5
• MNVCCKVPSGWSCN-RXMQYKEDSA-N (5r)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(C)=C(C(O)=O)N2C(=O)C[C@H]21 MNVCCKVPSGWSCN-RXMQYKEDSA-N 0.000 description 5
• DWDDFMFCVGDERN-UHFFFAOYSA-N 1-chloroazetidin-2-one Chemical compound ClN1CCC1=O DWDDFMFCVGDERN-UHFFFAOYSA-N 0.000 description 5
• SUHXTVABLHHRST-UHFFFAOYSA-N 2-azidoacetyl chloride Chemical compound ClC(=O)CN=[N+]=[N-] SUHXTVABLHHRST-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 239000005909 Kieselgur Substances 0.000 description 5
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