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최홍대(Hong Dae Choi),마정주(Jung Joo Ma) 대한약학회 1991 약학회지 Vol.35 No.2
A new method for the synthesis of butibufen, which is a non steroidal anti-inflammatory agent, is described. Friedel-Crafts reaction of isobutylbenzene with ethyl alpha-chloro-alpha-(methylthio) acetate (1) gives ethyl alpha-methylthio-(p-isobutylphenyl)acetate (2). Ethyl 2-methylthio-2-(4-isobutylphenyl)butyrate (3) is obtained from treatment of the compound (2) with NaH and EtI. Butibufen (5) is synthesized by reductive desulfurization of the compound (3) with zinc dust-acetic acid or Raney nickel, followed by hydrolysis of the resultant ethyl 2-(4-isobutylphenyl)butyrate (4).
최홍대(Hong Dae Choi),마정주(Jung Joo Ma) 대한약학회 1991 약학회지 Vol.35 No.2
A convenient method for the synthesis of ibuproxam, which is a non steroidal antiinflammatory agent, is reported. Friedel-Crafts reaction of isobutylbenzene with ethyl alpha-chloro-alpha-(methylthio)acetate (3) gives ethyl alpha-methylthio-(p-isobutylphenyl) acetate (4). Ethyl 2-methylthio-2-(4-isobutylphenyl) propionate (5) is obtained from methylation of the compound (4) with NaH and MeI. Ibuproxam (7) is easily synthesized by reductive desulfurization of the compound (5) with zinc dust-acetic acid or Raney nickel, followed by treatment of the resultant ethyl 2-(4-isobutylphenyl) propionate (6) with H2NOH-HCl.
최홍대(Hong Dae Choi),마정주(Jung Joo Ma) 대한약학회 1992 약학회지 Vol.36 No.4
A facile method for tolmetin, which is a potent antiinflammatory agent, is described. Friedel-Crafts reaction of 1-methylpyrrole with ethyl alpha-chloro-alpha-(methylthio)acetate (1) gave ethyl alpha-methylthio-1-methyl-2-pyrroleacetate (4), which was readily converted into ethyl 1-methyl-2-pyrroleacetate (5) by reductive desulfurization with zinc dust in acetic acid. Tolmetin was synthesized by Friedel-Crafts acylation of (5) with p-toluoyl chloride, followed by hydrolysis of the resultant ethyl 5-(p-toluoyl)-1-methylpyrrole-2-acetate (6).
최홍대(Hong Dae Choi),윤호상(Ho Sang Yun),강병원(Byung Won Kang),마정주(Jung Joo Ma),손병화(Byeng Wha Son) 대한약학회 1992 약학회지 Vol.36 No.1
A new method for the synthesis of alminoprofen, which is a non-steroidal antiinflammatory agent, was described. Ethyl 2-phenyl-propionate(4) was prepared by Friedel-Crafts reaction of benzene with ethyl alpha-chloro-alpha(methylthio)acetate(1), followed by methylation and desulfurization of the resultant ethyl 2-(methylthio)phenylacetate(2). Ethyl 2-(p-aminophenyl)propionate(6) was obtained by nitration of (4) and successive reduction of ethyl 2-(p-nitrophenyl)propionate(5). Alminoprofen was synthesized by reaction of (6) with methallyl chloride, followed by hydrolysis of the resultant ethyl 2-(p-methylallylaminophenyl)propionate(7).
최홍대(Hong Dae Choi),강병원(Byung Won Kang),마정주(Jung Joo Ma),윤호상(Ho Sang Yun) 대한약학회 1991 약학회지 Vol.35 No.4
A convenient method for the synthesis of indoprofen, which is a potent antiinflammatory agent, was described. Ethyl alpha-(4-aminophenyl)propionate was prepared by nitration of ethyl alpha-phenylpropionate, followed by reduction. Ethyl alpha-[4-(1,3-dioxo-2-iso-indolinyl)phenyl]propionate was obtained from condensation reaction of phthalic anhydride and ethyl alpha-(4-aminophenyl)propionate. Indoprofen was prepared by reduction of ethyl alpha-[3-(1,3-dioxo-2-iso-indolinyl)phenyl]propionate with zinc dust-acetic acid, followed by hydrolysis of the resultant ethyl alpha-[4-(l-oxo-2-iso-indolinyl)phenyl]propionate.
마정주,최홍대,강병원,윤호상 동의대학교 기초과학연구소 1992 基礎科學硏究論文集 Vol.2 No.1
A convenient method for the synthesis of indoprofen, which is a potent antiinflammatory agent, was described. Ethyl α-(4-aminophenyl)propionate was prepared by nitration of ethyl α-phenylpropionate, followed by reduction. Ethyl α-[4-(1,3-dioxo-2-iso-indolinyl)phenyl]propionate was obtained from condensation reaction of phthalic anhydride and ethyl α-(4-aminophenyl)propionate. Indoprofen was prepared by reduction of ethyl α-[3-(1,3-dioxo-2-iso-indolinyl)phenyl]propionate with zinc dust-acetic acid, followed by hydrolysis of the resultant ethyl α-[4-(1-oxo-2-iso-indolinyl)phenyl]propionate.
최홍대,강병원,마정주,윤호상,손병화 동의대학교 기초과학연구소 1993 基礎科學硏究論文集 Vol.3 No.1
A new method for the synthesis of alminoprofen, which is a non-steroidal antiinflammatory agent, was described. Ethyl 2-phenyl-propionate(4) was prepared by Friedel-Crafts reaction of benzene with ethyl α-chloro-α-methylthio)acetate(1), followed by methylation and desulfurization of the resultant ethyl 2-(methylthio)phenylacetate(2). Ethyl 2-(p-aminophenyl)propionate(6) was obtained by nitration of (4) and successive reduction of ethyl 2-(p-nitrophenyl)propionate(5). Alminoprofen was synthesized by reaction of (6) with methallyl chloride, followed by hydrolysis of the resultant ethyl 2-(p-methylallylaminophenyl)propionate (7).
최홍대,마정주 동의대학교 기초과학연구소 1992 基礎科學硏究論文集 Vol.2 No.1
A convenient method for the synthesis of ibuproxam, which is a non steroidal anti-inflammatory agent, is reported. Friedel-Crafts reaction of isobutylbenzene with ethyl α-chloro-α-(methylthio)acetate (3) gives ethyl α-methylthio-(p-isobutylpheny) acetate (4). Ethyl 2-methylthio-2-(4-isobutylphenyl) propionate (5) is obtained from methylation of the compound (4) with NaH and MeI. Ibuproxam (7) is easily synthesized by reductive desulfurization of the compound (5) with zinc dust-acetic acid or Raney nickel, followed by treatment of the resultant ethyl 2-(4-isobutyl-pheny) propionate (6) with H₂NOH·HCl.
최홍대,마정주 동의대학교 기초과학연구소 1993 基礎科學硏究論文集 Vol.3 No.1
A facile method for tolmetin, which is a potent antiinflammatory agent, is described. Friedel-Crafts reaction of 1-methylpyrrole with ethyl α-chloro-α-(methylthio)acetate (1) gave ethyl α-methylthio-1-methyl-2-pyrroleacetate (4), which was readily converted into ethyl 1-methyl-2-pyrroleacetate (5) by reductive desulfurization with zinc dust in acetic acid. Tolmetin was synthesized by Friedel-Crafts acylation of (5) with p-toluoyl chloride, followed by hydrolysis of the resultant ethly 5-(p-toluoyl)-1-methylpyrrole-2-acetate (6).
최홍대,마정주 동의대학교 기초과학연구소 1992 基礎科學硏究論文集 Vol.2 No.1
A new method for the synthesis of butibufen, which is a non steroidal anti-inflammatory agent, is described. Friedel-Crafts reaction of isoabutylbenzene with ethyl α-chloro-α-(methylthio)acetate (1) gives ethyl α-methylthio-(p-isobutylphenyl)acetate (2).Ethyl 2-methylthio-2-(4-isobutylphenyl)butyrate (3) is obtained from treatment of the compound (2) with NaH and EtI. Butibufen (5) is synthesized by reductive desulfurization of the compound (3) with zinc dust-acetic acid or Raney nickel, followed by hydrolysis of the resultant ethyl 2-(4-isobutylphenyl)butyrate (4).