NO831034L - Fremgangsmaate til fremstilling av nye derivater av indolizino(8,7-b)-indoler. - Google Patents

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Publication number

NO831034L

NO831034L NO831034A NO831034A NO831034L NO 831034 L NO831034 L NO 831034L NO 831034 A NO831034 A NO 831034A NO 831034 A NO831034 A NO 831034A NO 831034 L NO831034 L NO 831034L

Authority

NO

Norway

Prior art keywords

group

formula

hydrogen

compound

hydroxy

Prior art date

1982-03-24

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• 238000000034 method Methods 0.000 title claims description 85
• 238000002360 preparation method Methods 0.000 title claims description 24
• 150000002475 indoles Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 311
• -1 benzyloxymethyl Chemical group 0.000 claims description 213
• 239000001257 hydrogen Substances 0.000 claims description 161
• 229910052739 hydrogen Inorganic materials 0.000 claims description 161
• 125000000217 alkyl group Chemical group 0.000 claims description 133
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
• 239000002253 acid Substances 0.000 claims description 92
• 150000003839 salts Chemical class 0.000 claims description 86
• 150000002431 hydrogen Chemical class 0.000 claims description 82
• 239000000203 mixture Substances 0.000 claims description 73
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 73
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
• 125000003277 amino group Chemical group 0.000 claims description 52
• 125000006239 protecting group Chemical group 0.000 claims description 50
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
• 230000009467 reduction Effects 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 43
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 41
• OSWNOVFZARRSKM-UHFFFAOYSA-N 3-indol-1-ylpropanoic acid Chemical compound C1=CC=C2N(CCC(=O)O)C=CC2=C1 OSWNOVFZARRSKM-UHFFFAOYSA-N 0.000 claims description 40
• 229910052740 iodine Inorganic materials 0.000 claims description 32
• 125000002837 carbocyclic group Chemical group 0.000 claims description 31
• 230000008569 process Effects 0.000 claims description 24
• 230000007062 hydrolysis Effects 0.000 claims description 22
• 238000006460 hydrolysis reaction Methods 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 238000003776 cleavage reaction Methods 0.000 claims description 16
• 231100000252 nontoxic Toxicity 0.000 claims description 16
• 230000003000 nontoxic effect Effects 0.000 claims description 16
• 230000007017 scission Effects 0.000 claims description 16
• 238000012546 transfer Methods 0.000 claims description 16
• 230000003287 optical effect Effects 0.000 claims description 15
• CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 150000001204 N-oxides Chemical class 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 238000003797 solvolysis reaction Methods 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 238000006136 alcoholysis reaction Methods 0.000 claims description 6
• 238000005915 ammonolysis reaction Methods 0.000 claims description 6
• 150000001450 anions Chemical class 0.000 claims description 6
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 5
• 238000007098 aminolysis reaction Methods 0.000 claims description 4
• YAMNPRZWDUBVQI-UHFFFAOYSA-N 11h-indolizino[8,7-b]indole Chemical class N1C2=CC=CC=C2C2=C1C1=CC=CN1C=C2 YAMNPRZWDUBVQI-UHFFFAOYSA-N 0.000 claims description 3
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
• 238000009740 moulding (composite fabrication) Methods 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
• 239000000243 solution Substances 0.000 description 131
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 95
• 238000006243 chemical reaction Methods 0.000 description 87
• 235000002639 sodium chloride Nutrition 0.000 description 87
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
• 238000002844 melting Methods 0.000 description 68
• 230000008018 melting Effects 0.000 description 68
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
• 238000001816 cooling Methods 0.000 description 54
• 239000002904 solvent Substances 0.000 description 48
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
• 239000003795 chemical substances by application Substances 0.000 description 42
• 238000006722 reduction reaction Methods 0.000 description 38
• 239000000126 substance Substances 0.000 description 38
• 229910052757 nitrogen Inorganic materials 0.000 description 37
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• 238000003756 stirring Methods 0.000 description 36
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
• 125000003545 alkoxy group Chemical group 0.000 description 33
• 230000002378 acidificating effect Effects 0.000 description 32
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
• 235000011121 sodium hydroxide Nutrition 0.000 description 31
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
• 235000019441 ethanol Nutrition 0.000 description 30
• 239000003054 catalyst Substances 0.000 description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 27
• 239000007858 starting material Substances 0.000 description 25
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 24
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 24
• BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 24
• 125000002252 acyl group Chemical group 0.000 description 23
• 229910052783 alkali metal Inorganic materials 0.000 description 23
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 23
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 22
• 239000002585 base Substances 0.000 description 21
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 21
• 239000000460 chlorine Substances 0.000 description 21
• 229910052801 chlorine Inorganic materials 0.000 description 21
• 239000012074 organic phase Substances 0.000 description 21
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
• 150000001340 alkali metals Chemical class 0.000 description 19
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 19
• 229910052794 bromium Inorganic materials 0.000 description 19
• 150000002148 esters Chemical class 0.000 description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 18
• 230000002829 reductive effect Effects 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
• 239000012299 nitrogen atmosphere Substances 0.000 description 17
• 229910052938 sodium sulfate Inorganic materials 0.000 description 17
• 235000011152 sodium sulphate Nutrition 0.000 description 17
• 229960000583 acetic acid Drugs 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 15
• 239000012298 atmosphere Substances 0.000 description 15
• 229960002922 vinburnine Drugs 0.000 description 15
• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 14
• 239000013543 active substance Substances 0.000 description 14
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
• 150000007513 acids Chemical class 0.000 description 13
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 13
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
• 125000003118 aryl group Chemical group 0.000 description 12
• 150000004820 halides Chemical group 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
• 241001465754 Metazoa Species 0.000 description 11
• 125000004423 acyloxy group Chemical group 0.000 description 11
• 125000003282 alkyl amino group Chemical group 0.000 description 11
• 125000005237 alkyleneamino group Chemical group 0.000 description 11
• 125000001118 alkylidene group Chemical group 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• 239000003638 chemical reducing agent Substances 0.000 description 11
• 238000009833 condensation Methods 0.000 description 11
• 230000005494 condensation Effects 0.000 description 11
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 11
• 239000011261 inert gas Substances 0.000 description 11
• 229910052500 inorganic mineral Inorganic materials 0.000 description 11
• 235000010755 mineral Nutrition 0.000 description 11
• 239000011707 mineral 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
• 239000007795 chemical reaction product Substances 0.000 description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
• ILAGLZFPDDPGEI-UHFFFAOYSA-N methyl 3-indol-1-ylpropanoate Chemical compound C1=CC=C2N(CCC(=O)OC)C=CC2=C1 ILAGLZFPDDPGEI-UHFFFAOYSA-N 0.000 description 10
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 235000015424 sodium Nutrition 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 238000010438 heat treatment Methods 0.000 description 9
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 9
• 239000012452 mother liquor Substances 0.000 description 9
• 150000007524 organic acids Chemical class 0.000 description 9
• 238000010626 work up procedure Methods 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 125000001931 aliphatic group Chemical group 0.000 description 8
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 8
• 229910021529 ammonia Inorganic materials 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• 238000001704 evaporation Methods 0.000 description 8
• 238000005984 hydrogenation reaction Methods 0.000 description 8
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• 241000699670 Mus sp. Species 0.000 description 7
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
• 229920002472 Starch Polymers 0.000 description 7
• 125000005236 alkanoylamino group Chemical group 0.000 description 7
• 235000011114 ammonium hydroxide Nutrition 0.000 description 7
• 239000011230 binding agent Substances 0.000 description 7
• 230000008020 evaporation Effects 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 150000004678 hydrides Chemical class 0.000 description 7
• 150000007522 mineralic acids Chemical class 0.000 description 7
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 230000007306 turnover Effects 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
• 239000007868 Raney catalyst Substances 0.000 description 6
• 229910000564 Raney nickel Inorganic materials 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 125000003172 aldehyde group Chemical group 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 125000005333 aroyloxy group Chemical group 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• 238000000354 decomposition reaction Methods 0.000 description 6
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
• VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 6
• 239000012280 lithium aluminium hydride Substances 0.000 description 6
• 229940098779 methanesulfonic acid Drugs 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 239000011591 potassium Substances 0.000 description 6
• 229910052700 potassium Inorganic materials 0.000 description 6
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
• CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 5
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
• 125000005115 alkyl carbamoyl group Chemical group 0.000 description 5
• 125000005530 alkylenedioxy group Chemical group 0.000 description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
• 150000002736 metal compounds Chemical class 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 239000000825 pharmaceutical preparation Substances 0.000 description 5
• 239000004033 plastic Substances 0.000 description 5
• 229920003023 plastic Polymers 0.000 description 5
• 229910052697 platinum Inorganic materials 0.000 description 5
• 230000001681 protective effect Effects 0.000 description 5
• 150000003335 secondary amines Chemical class 0.000 description 5
• 230000035939 shock Effects 0.000 description 5
• 239000012279 sodium borohydride Substances 0.000 description 5
• 229910000033 sodium borohydride Inorganic materials 0.000 description 5
• 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 5
• 239000011592 zinc chloride Substances 0.000 description 5
• 235000005074 zinc chloride Nutrition 0.000 description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
• XXKBCTFARZSEHZ-UHFFFAOYSA-N 4-chloro-2-ethylbutanoyl chloride Chemical compound CCC(C(Cl)=O)CCCl XXKBCTFARZSEHZ-UHFFFAOYSA-N 0.000 description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
• BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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