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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).
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 1991 基礎科學硏究論文集 Vol.1 No.1
A new synthetic method for bufexamac, which is a potent anti-inflammatory agent, was described. Friedel-Crafts reaction of butoxybenzene (2) with ethyl α-chloro-α-(methylthio)acetate (1) gave ethyl 2-methylthio-2-(ρ-butoxyphenyl) acetate (3) Ethyl 2-(ρ-butoxyphenyl)acetate (4) was prepared by desulfurization of compound (3) with zinc dust-acetic acid. Bufexamac (5) could be easily synthesized by treatment of compound (4) with hydroxylamine·HCl.
항류우머티즘 물질인 p-(아세틸아미노)페닐아세트산의 합성
최홍대,손병화 동의대학교 기초과학연구소 1998 基礎科學硏究論文集 Vol.8 No.1
The efficient synthesis of p-(acetylamino)phenylacetic acid(7), a antirheumatic agent, is reported. Methyl phenylacetate(3) was prepared from Friedel- Crafts reaction of benzene with methyl α-chloro-α-(methylthio)acetate(1) followed by reductive desulfurization with zinc dust in acetic acid. Compound(7) was obtained from 3 by a sequence of nitration, reduction. N-acylation, and hydrolysis.