DE2132883A1 - Cephemverbindungen - Google Patents

Info

Publication number

DE2132883A1

DE2132883A1 DE19712132883 DE2132883A DE2132883A1 DE 2132883 A1 DE2132883 A1 DE 2132883A1 DE 19712132883 DE19712132883 DE 19712132883 DE 2132883 A DE2132883 A DE 2132883A DE 2132883 A1 DE2132883 A1 DE 2132883A1

Authority

DE

Germany

Prior art keywords

amino

radical

carboxylic acid

compounds

group

Prior art date

1970-07-08

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

Links

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• -1 Cephem compounds Chemical class 0.000 title claims description 841
• 150000001875 compounds Chemical class 0.000 claims description 311
• 238000000034 method Methods 0.000 claims description 245
• 229910052739 hydrogen Inorganic materials 0.000 claims description 235
• 239000001257 hydrogen Substances 0.000 claims description 233
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 215
• 150000003254 radicals Chemical class 0.000 claims description 173
• 150000003839 salts Chemical class 0.000 claims description 156
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 147
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 142
• 239000002253 acid Substances 0.000 claims description 114
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 104
• 125000003545 alkoxy group Chemical group 0.000 claims description 96
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 85
• 239000003795 chemical substances by application Substances 0.000 claims description 85
• 230000002378 acidificating effect Effects 0.000 claims description 84
• 125000000217 alkyl group Chemical group 0.000 claims description 83
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 82
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 78
• 239000000203 mixture Substances 0.000 claims description 76
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 60
• 239000003638 chemical reducing agent Substances 0.000 claims description 58
• 125000003118 aryl group Chemical group 0.000 claims description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
• 125000003277 amino group Chemical group 0.000 claims description 55
• 125000004414 alkyl thio group Chemical group 0.000 claims description 54
• 125000002252 acyl group Chemical group 0.000 claims description 53
• 125000001424 substituent group Chemical group 0.000 claims description 53
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
• 230000002829 reductive effect Effects 0.000 claims description 49
• 125000003282 alkyl amino group Chemical group 0.000 claims description 48
• 230000008569 process Effects 0.000 claims description 47
• 239000007858 starting material Substances 0.000 claims description 45
• 229910052799 carbon Inorganic materials 0.000 claims description 44
• 238000006243 chemical reaction Methods 0.000 claims description 44
• 150000002431 hydrogen Chemical class 0.000 claims description 43
• 230000007935 neutral effect Effects 0.000 claims description 40
• 125000005843 halogen group Chemical group 0.000 claims description 38
• 125000004423 acyloxy group Chemical group 0.000 claims description 37
• 125000006239 protecting group Chemical group 0.000 claims description 37
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
• 150000002148 esters Chemical class 0.000 claims description 32
• 230000004962 physiological condition Effects 0.000 claims description 30
• 150000001721 carbon Chemical group 0.000 claims description 29
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 28
• 229930195733 hydrocarbon Natural products 0.000 claims description 28
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 26
• 239000004215 Carbon black (E152) Substances 0.000 claims description 25
• 125000002619 bicyclic group Chemical group 0.000 claims description 25
• 125000001544 thienyl group Chemical group 0.000 claims description 25
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 21
• 230000000269 nucleophilic effect Effects 0.000 claims description 21
• 239000002841 Lewis acid Substances 0.000 claims description 20
• 150000007517 lewis acids Chemical class 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
• RJFPBECTFIUTHB-BAFYGKSASA-N (6r)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC=C(C(O)=O)N2C(=O)C(N)[C@H]21 RJFPBECTFIUTHB-BAFYGKSASA-N 0.000 claims description 18
• 150000007513 acids Chemical class 0.000 claims description 18
• 125000002541 furyl group Chemical group 0.000 claims description 17
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 16
• 239000000543 intermediate Substances 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
• 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 14
• 150000001735 carboxylic acids Chemical class 0.000 claims description 14
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 12
• 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 239000011630 iodine Substances 0.000 claims description 11
• 229910052751 metal Inorganic materials 0.000 claims description 11
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 239000011737 fluorine Substances 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 238000006722 reduction reaction Methods 0.000 claims description 10
• ZPKLKQNMZTUIFZ-UHFFFAOYSA-N 2-phenylethanone Chemical compound O=[C]CC1=CC=CC=C1 ZPKLKQNMZTUIFZ-UHFFFAOYSA-N 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 9
• 230000003213 activating effect Effects 0.000 claims description 9
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 230000009467 reduction Effects 0.000 claims description 9
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
• 125000005042 acyloxymethyl group Chemical group 0.000 claims description 8
• 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 claims description 8
• 238000006317 isomerization reaction Methods 0.000 claims description 8
• NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 7
• 239000000463 material Substances 0.000 claims description 7
• 150000007522 mineralic acids Chemical class 0.000 claims description 7
• 150000007524 organic acids Chemical class 0.000 claims description 7
• 230000003647 oxidation Effects 0.000 claims description 7
• 238000007254 oxidation reaction Methods 0.000 claims description 7
• 229910052698 phosphorus Inorganic materials 0.000 claims description 7
• SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical group S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims description 6
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 6
• 230000007062 hydrolysis Effects 0.000 claims description 6
• 238000006460 hydrolysis reaction Methods 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 239000011574 phosphorus Substances 0.000 claims description 6
• 229910052710 silicon Inorganic materials 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 229910052718 tin Inorganic materials 0.000 claims description 6
• 238000003776 cleavage reaction Methods 0.000 claims description 5
• 239000010949 copper Substances 0.000 claims description 5
• 239000013067 intermediate product Substances 0.000 claims description 5
• 239000007800 oxidant agent Substances 0.000 claims description 5
• 230000007017 scission Effects 0.000 claims description 5
• 150000003460 sulfonic acids Chemical class 0.000 claims description 5
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052802 copper Inorganic materials 0.000 claims description 4
• 230000003301 hydrolyzing effect Effects 0.000 claims description 4
• 150000004966 inorganic peroxy acids Chemical class 0.000 claims description 4
• 229910052742 iron Inorganic materials 0.000 claims description 4
• 150000004967 organic peroxy acids Chemical class 0.000 claims description 4
• 239000000376 reactant Substances 0.000 claims description 4
• 239000010703 silicon Substances 0.000 claims description 4
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
• GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 3
• 150000002484 inorganic compounds Chemical class 0.000 claims description 3
• 229910052748 manganese Inorganic materials 0.000 claims description 3
• 239000011572 manganese Substances 0.000 claims description 3
• 150000004681 metal hydrides Chemical class 0.000 claims description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
• 150000002903 organophosphorus compounds Chemical class 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 2
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
• 229910052987 metal hydride Inorganic materials 0.000 claims description 2
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 35
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims 12
• NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims 5
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
• JDWXXPODXLMMJS-VUYXPMRHSA-N (5r)-6-amino-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound S1CC(C(O)=O)N2C(=O)C(N)[C@H]21 JDWXXPODXLMMJS-VUYXPMRHSA-N 0.000 claims 3
• DGJSPZSLNNDPQC-ZMMDDIOLSA-N (6r)-5-oxo-5$l^{4}-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class C1=CCS(=O)[C@H]2N1C(=O)C2 DGJSPZSLNNDPQC-ZMMDDIOLSA-N 0.000 claims 3
• 230000001590 oxidative effect Effects 0.000 claims 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims 3
• RYYITAGXGLVQNL-HPKQAEFZSA-N (6R,7R)-4-amino-3-[(4-hydroxyphenyl)methyl]-8-oxo-7-(2-phenylacetyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC1=CC=C(CC=2C(S[C@H]3N(C=2C(=O)O)C([C@H]3C(CC2=CC=CC=C2)=O)=O)N)C=C1 RYYITAGXGLVQNL-HPKQAEFZSA-N 0.000 claims 2
• 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 2
• 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
• 239000011135 tin Substances 0.000 claims 2
• TWSWWXRDKDIIGK-OXPKRCOGSA-N (6R,7R)-4-amino-3-[(5-methoxycarbonylfuran-2-yl)methyl]-8-oxo-7-(2-thiophen-2-ylacetyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound COC(=O)C1=CC=C(CC=2C(S[C@H]3N(C=2C(=O)O)C([C@H]3C(CC=2SC=CC=2)=O)=O)N)O1 TWSWWXRDKDIIGK-OXPKRCOGSA-N 0.000 claims 1
• QITDACOZCQXYQY-BAFYGKSASA-N (6r)-7-amino-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C(N)[C@H]21 QITDACOZCQXYQY-BAFYGKSASA-N 0.000 claims 1
• RCPSPKMNAWQBQZ-VQIMIIECSA-N (6r,7r)-3-[(5-carboxyfuran-2-yl)methyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC=3C=CC=CC=3)[C@H]2SC1 RCPSPKMNAWQBQZ-VQIMIIECSA-N 0.000 claims 1
• ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 claims 1
• LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
• TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims 1
• YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims 1
• 206010000210 abortion Diseases 0.000 claims 1
• 239000008186 active pharmaceutical agent Substances 0.000 claims 1
• YKTAWRASWMSDFW-RUZDIDTESA-N benzhydryl (6R)-8-oxo-3-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C1=C(CS[C@H]2N1C(C2)=O)NC(CC1=CC=CC=C1)=O YKTAWRASWMSDFW-RUZDIDTESA-N 0.000 claims 1
• 230000001747 exhibiting effect Effects 0.000 claims 1
• 210000003608 fece Anatomy 0.000 claims 1
• 239000003337 fertilizer Substances 0.000 claims 1
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
• 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
• SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims 1
• 230000006698 induction Effects 0.000 claims 1
• 229910052759 nickel Chemical group 0.000 claims 1
• LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 1
• 238000009938 salting Methods 0.000 claims 1
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• 229940116269 uric acid Drugs 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 259
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 169
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 127
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 113
• 239000000243 solution Substances 0.000 description 111
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
• 229960000583 acetic acid Drugs 0.000 description 57
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 51
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 44
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 42
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
• 125000001931 aliphatic group Chemical group 0.000 description 38
• 239000010410 layer Substances 0.000 description 36
• 239000000741 silica gel Substances 0.000 description 35
• 229910002027 silica gel Inorganic materials 0.000 description 35
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• 238000000862 absorption spectrum Methods 0.000 description 29
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 25
• 229910052736 halogen Inorganic materials 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• 150000002367 halogens Chemical class 0.000 description 22
• 235000011007 phosphoric acid Nutrition 0.000 description 22
• 239000011780 sodium chloride Substances 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 21
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 20
• 229910052801 chlorine Inorganic materials 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 20
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
• 125000000623 heterocyclic group Chemical group 0.000 description 19
• 229910052757 nitrogen Inorganic materials 0.000 description 19
• 239000002904 solvent Substances 0.000 description 19
• 239000000047 product Substances 0.000 description 18
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
• 239000000284 extract Substances 0.000 description 17
• 239000000155 melt Substances 0.000 description 17
• 238000007792 addition Methods 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
• 239000002480 mineral oil Substances 0.000 description 16
• 235000010446 mineral oil Nutrition 0.000 description 16
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
• 239000008346 aqueous phase Substances 0.000 description 15
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