DE2530339A1 - N-substituierte aminomethyl-methoxyheterocyclen - Google Patents

Info

Publication number

DE2530339A1

DE2530339A1 DE19752530339 DE2530339A DE2530339A1 DE 2530339 A1 DE2530339 A1 DE 2530339A1 DE 19752530339 DE19752530339 DE 19752530339 DE 2530339 A DE2530339 A DE 2530339A DE 2530339 A1 DE2530339 A1 DE 2530339A1

Authority

DE

Germany

Prior art keywords

formula

group

radical

acid

methyl

Prior art date

1974-07-12

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.)

Pending

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• -1 3-cephem compound Chemical class 0.000 claims description 345
• 150000001875 compounds Chemical class 0.000 claims description 149
• 125000003277 amino group Chemical group 0.000 claims description 137
• 150000001735 carboxylic acids Chemical class 0.000 claims description 125
• 239000002253 acid Substances 0.000 claims description 118
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 110
• 150000003254 radicals Chemical class 0.000 claims description 97
• 150000003839 salts Chemical class 0.000 claims description 93
• 125000000217 alkyl group Chemical group 0.000 claims description 85
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 79
• 238000000034 method Methods 0.000 claims description 77
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
• 239000007858 starting material Substances 0.000 claims description 59
• 239000003795 chemical substances by application Substances 0.000 claims description 57
• 238000006243 chemical reaction Methods 0.000 claims description 42
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 40
• 229910052799 carbon Inorganic materials 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 34
• 229910052717 sulfur Inorganic materials 0.000 claims description 34
• 239000002585 base Substances 0.000 claims description 33
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 30
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 29
• 239000011593 sulfur Substances 0.000 claims description 29
• 239000000203 mixture Substances 0.000 claims description 28
• 238000005917 acylation reaction Methods 0.000 claims description 26
• 230000010933 acylation Effects 0.000 claims description 24
• 150000002148 esters Chemical class 0.000 claims description 24
• 239000000460 chlorine Substances 0.000 claims description 23
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
• 150000001721 carbon Chemical group 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 239000001301 oxygen Substances 0.000 claims description 22
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
• 229910052783 alkali metal Inorganic materials 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000004429 atom Chemical group 0.000 claims description 19
• 239000003638 chemical reducing agent Substances 0.000 claims description 19
• 125000000524 functional group Chemical group 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
• 150000007513 acids Chemical class 0.000 claims description 18
• 150000008064 anhydrides Chemical class 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000006239 protecting group Chemical group 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 16
• FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims description 15
• 125000001931 aliphatic group Chemical group 0.000 claims description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
• 230000000269 nucleophilic effect Effects 0.000 claims description 14
• 150000001340 alkali metals Chemical class 0.000 claims description 13
• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000004423 acyloxy group Chemical group 0.000 claims description 11
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 11
• 150000007530 organic bases Chemical class 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 229930195733 hydrocarbon Natural products 0.000 claims description 10
• 229910052744 lithium Inorganic materials 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 230000002829 reductive effect Effects 0.000 claims description 10
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 229910052698 phosphorus Inorganic materials 0.000 claims description 9
• 239000004215 Carbon black (E152) Substances 0.000 claims description 8
• 150000003973 alkyl amines Chemical class 0.000 claims description 8
• 125000005002 aryl methyl group Chemical group 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 125000001453 quaternary ammonium group Chemical group 0.000 claims description 8
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 7
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000005110 aryl thio group Chemical group 0.000 claims description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
• 231100000252 nontoxic Toxicity 0.000 claims description 7
• 230000003000 nontoxic effect Effects 0.000 claims description 7
• 239000011574 phosphorus Substances 0.000 claims description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 7
• 239000004332 silver Substances 0.000 claims description 7
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 6
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
• 229910052709 silver Inorganic materials 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
• 230000003115 biocidal effect Effects 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 239000012433 hydrogen halide Substances 0.000 claims description 5
• 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
• 239000013067 intermediate product Substances 0.000 claims description 5
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
• 230000004962 physiological condition Effects 0.000 claims description 5
• 238000003797 solvolysis reaction Methods 0.000 claims description 5
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
• WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 claims description 4
• 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• 239000002262 Schiff base Substances 0.000 claims description 3
• 150000004753 Schiff bases Chemical class 0.000 claims description 3
• 150000004703 alkoxides Chemical class 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
• 230000003009 desulfurizing effect Effects 0.000 claims description 3
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
• 125000002524 organometallic group Chemical group 0.000 claims description 3
• 125000000369 oxido group Chemical group [*]=O 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000005237 alkyleneamino group Chemical group 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 150000002009 diols Chemical class 0.000 claims description 2
• 239000003337 fertilizer Substances 0.000 claims description 2
• 150000002513 isocyanates Chemical class 0.000 claims description 2
• 229940100892 mercury compound Drugs 0.000 claims description 2
• 150000002731 mercury compounds Chemical class 0.000 claims description 2
• 229910000474 mercury oxide Inorganic materials 0.000 claims description 2
• BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 2
• UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 2
• 229920000642 polymer Polymers 0.000 claims description 2
• 230000001681 protective effect Effects 0.000 claims description 2
• 229910001923 silver oxide Inorganic materials 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims 2
• 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 1
• 241000238876 Acari Species 0.000 claims 1
• 241000195493 Cryptophyta Species 0.000 claims 1
• 241001214714 Niea Species 0.000 claims 1
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
• JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims 1
• 229940100890 silver compound Drugs 0.000 claims 1
• 125000004354 sulfur functional group Chemical group 0.000 claims 1
• 150000003510 tertiary aliphatic amines Chemical class 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 70
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• 239000000243 solution Substances 0.000 description 25
• 239000002904 solvent Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
• 150000004820 halides Chemical class 0.000 description 17
• 229910052751 metal Inorganic materials 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
• 239000002184 metal Substances 0.000 description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
• 239000011261 inert gas Substances 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
• 230000002378 acidificating effect Effects 0.000 description 12
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
• 229910052794 bromium Inorganic materials 0.000 description 12
• 238000001816 cooling Methods 0.000 description 12
• 230000007062 hydrolysis Effects 0.000 description 12
• 238000006460 hydrolysis reaction Methods 0.000 description 12
• 239000012299 nitrogen atmosphere Substances 0.000 description 12
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 12
• 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 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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 11
• 239000003054 catalyst Substances 0.000 description 11
• 238000010438 heat treatment Methods 0.000 description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• 239000003085 diluting agent Substances 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• 239000003153 chemical reaction reagent Substances 0.000 description 9
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• 238000000338 in vitro Methods 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
• 238000000862 absorption spectrum Methods 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 7
• 238000003776 cleavage reaction Methods 0.000 description 7
• 235000019253 formic acid Nutrition 0.000 description 7
• 229910052740 iodine Inorganic materials 0.000 description 7
• 150000002576 ketones Chemical class 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 238000006722 reduction reaction Methods 0.000 description 7
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
• 229910052500 inorganic mineral Inorganic materials 0.000 description 6
• 150000002736 metal compounds Chemical class 0.000 description 6
• 235000010755 mineral Nutrition 0.000 description 6
• 239000011707 mineral Substances 0.000 description 6
• 239000012434 nucleophilic reagent Substances 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
• 239000011541 reaction mixture Substances 0.000 description 6
• 230000007017 scission Effects 0.000 description 6
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 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
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
• 230000003213 activating effect Effects 0.000 description 5
• 239000003513 alkali Substances 0.000 description 5
• 150000003863 ammonium salts Chemical class 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• 239000011737 fluorine Substances 0.000 description 5
• 150000007522 mineralic acids Chemical class 0.000 description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 239000011780 sodium chloride Substances 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 229910052725 zinc Inorganic materials 0.000 description 5
• 239000011701 zinc Substances 0.000 description 5
• WSNDAYQNZRJGMJ-UHFFFAOYSA-N 2,2,2-trifluoroethanone Chemical compound FC(F)(F)[C]=O WSNDAYQNZRJGMJ-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
• 108020004256 Beta-lactamase Proteins 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
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