SU399107A1 - - Google Patents

Info

Publication number

SU399107A1

SU399107A1 SU1262629A SU1262629A SU399107A1 SU 399107 A1 SU399107 A1 SU 399107A1 SU 1262629 A SU1262629 A SU 1262629A SU 1262629 A SU1262629 A SU 1262629A SU 399107 A1 SU399107 A1 SU 399107A1

Authority

SU

USSR - Soviet Union

Prior art keywords

carboxylic acid

benzofuran

methyl

methylenebutyryl

acid

Prior art date

Links

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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• 150000001875 compounds Chemical class 0.000 description 6
• -1 Heterocyclic Carboxylic Acids Chemical class 0.000 description 5
• 125000000217 alkyl group Chemical group 0.000 description 5
• 238000000034 method Methods 0.000 description 5
• 239000000243 solution Substances 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• 239000011737 fluorine Substances 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 150000003839 salts Chemical class 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 239000002585 base Substances 0.000 description 3
• 239000001257 hydrogen Substances 0.000 description 3
• 229910052739 hydrogen Inorganic materials 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 235000019439 ethyl acetate Nutrition 0.000 description 2
• DLTWLXUYSLIIQN-UHFFFAOYSA-N furacrinic acid Chemical compound C1=C(C)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)=C2 DLTWLXUYSLIIQN-UHFFFAOYSA-N 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 230000020477 pH reduction Effects 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• VIGUYDRUQODLPN-UHFFFAOYSA-N 3,4-dichloro-1-methyl-5-(2-methylidenebutanoyl)indole-2-carboxylic acid Chemical compound CN1C(=C(C2=C(C(=CC=C12)C(C(CC)=C)=O)Cl)Cl)C(=O)O VIGUYDRUQODLPN-UHFFFAOYSA-N 0.000 description 1
• CYTFMBZVPUBGMY-UHFFFAOYSA-N 3,6-dimethyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(OC2=C1C=C(C(=C2)C)C(C(CC)=C)=O)C(=O)O CYTFMBZVPUBGMY-UHFFFAOYSA-N 0.000 description 1
• YVEZTZZKJXJOEF-UHFFFAOYSA-N 4,6-dimethyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C(=CC2=C1C=C(O2)C(=O)O)C)C(C(CC)=C)=O YVEZTZZKJXJOEF-UHFFFAOYSA-N 0.000 description 1
• IPBNJWPJVRBOCK-UHFFFAOYSA-N 4-methyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C=CC2=C1C=C(O2)C(=O)O)C(C(CC)=C)=O IPBNJWPJVRBOCK-UHFFFAOYSA-N 0.000 description 1
• UWWHJLKVWYOXKR-UHFFFAOYSA-N 5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C=CC2=C(C=C(O2)C(=O)O)C1)CC UWWHJLKVWYOXKR-UHFFFAOYSA-N 0.000 description 1
• FTWKTEYMZJWOSZ-UHFFFAOYSA-N 6-chloro-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C(=CC2=C(C=C(O2)C(=O)O)C1)Cl)CC FTWKTEYMZJWOSZ-UHFFFAOYSA-N 0.000 description 1
• FRPJVIKXPDPKEW-UHFFFAOYSA-N 6-ethoxy-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C(C)OC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(CC)=C)=O FRPJVIKXPDPKEW-UHFFFAOYSA-N 0.000 description 1
• JYVZRRLDAFCFJH-UHFFFAOYSA-N 6-ethyl-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C(C)C1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(CC)=C)=O JYVZRRLDAFCFJH-UHFFFAOYSA-N 0.000 description 1
• NRQCYWFYNWDXDP-UHFFFAOYSA-N 6-methoxy-5-(2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound C1=C(OC)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)=C2 NRQCYWFYNWDXDP-UHFFFAOYSA-N 0.000 description 1
• PSBUPVYEUWGKHS-UHFFFAOYSA-N 6-methoxy-5-(2-methylprop-2-enoyl)-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(C)=C)=O PSBUPVYEUWGKHS-UHFFFAOYSA-N 0.000 description 1
• UKNLZJGUUXBXPU-UHFFFAOYSA-N 6-methyl-5-(2-methylidenepentanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(CCC)=C)=O UKNLZJGUUXBXPU-UHFFFAOYSA-N 0.000 description 1
• DLCASBFCJDKEJT-UHFFFAOYSA-N 6-methyl-5-(2-methylprop-2-enoyl)-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)C)=CC2=C1OC(C(O)=O)=C2 DLCASBFCJDKEJT-UHFFFAOYSA-N 0.000 description 1
• VMQDSECUDLRTDK-UHFFFAOYSA-N 6-methyl-5-(3-methyl-2-methylidenebutanoyl)-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC2=C(C=C(O2)C(=O)O)C=C1C(C(C(C)C)=C)=O VMQDSECUDLRTDK-UHFFFAOYSA-N 0.000 description 1
• GVBRVJZOXXPFLR-UHFFFAOYSA-N CC(C(C(C=CC1=C2C=C(C(O)=O)S1)=C2Cl)=O)=C Chemical compound CC(C(C(C=CC1=C2C=C(C(O)=O)S1)=C2Cl)=O)=C GVBRVJZOXXPFLR-UHFFFAOYSA-N 0.000 description 1
• GJVQPEVJKAYSFZ-UHFFFAOYSA-N CCC(C(C(C=CC1=C2C(Cl)=C(C(O)=O)O1)=C2Cl)=O)=C Chemical compound CCC(C(C(C=CC1=C2C(Cl)=C(C(O)=O)O1)=C2Cl)=O)=C GJVQPEVJKAYSFZ-UHFFFAOYSA-N 0.000 description 1
• 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
• 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 1
• 229930040373 Paraformaldehyde Natural products 0.000 description 1
• 229960000583 acetic acid Drugs 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000012362 glacial acetic acid Substances 0.000 description 1
• 125000001841 imino group Chemical group [H]N=* 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• 150000007530 organic bases Chemical group 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229920002866 paraformaldehyde Polymers 0.000 description 1
• 150000004965 peroxy acids Chemical class 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1