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항류우머티즘 물질인 p-(아세틸아미노)페닐아세트산의 합성
최홍대(Hong Dae Choi),손병화(Byung Wha Son) 대한약학회 1997 약학회지 Vol.41 No.4
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 alpha-chloro-alpha-(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.
최홍대(Hong Dae Choi) 대한약학회 1988 약학회지 Vol.32 No.5
New synthetic method for ibuprofen, which is a potent antiinflammatory agent, was described. Ethyl alpha-methylthio-p-isobutylphenylacetate was obtained from Friedel-Crafts reaction of isobutylbenzene with ethyl alpha-chloro-alpha-(methylthio)acetate in the presence of SnCl4. Ibuprofen was prepared in good yield by treatment of ethyl alpha-methylthio-p-isobutylphenylacetate with NaH and MeI, followed by desulfurization with zinc dust-acetic acid and hydrolysis of the resultant ethyl 2-methylthio-2-(4-isobutylphenyl)propionate.
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).
메틸 2-클로로-2-(메틸티오)아세트산을 이용한 치환페놀류로부터 2(3H)-벤조푸란온 유도체의 합성
최홍대(Hong Dae Choi),김미헌(Mi Heun Kim),신상훈(Sang Hoon Shin),손병화(Byung Wha Son) 대한약학회 1996 약학회지 Vol.40 No.6
5-Alkyl-2(3H)-benzofuranones(3a-e) were prepared from Friedel-Crafts reaction of 4-alkylphenols with methyl 2-chloro-2-(methylthio)acetae(1) followed by the treatment of zinc dust-acetic acid. The reaction of disubstituted phenols with 1 in the presence of stannic chloride afforded 3-methyltWa-2(3H)-benzofuranone derivatives(11a-c), which were readily converted into 2(3H)-benzofuranone derivatives(12a-c) by desulfurization with zinc dust-acetic acid.
최홍대(Hong Dae Choi),윤호상(Ho Sang Yun),강병원(Byung Won Kang) 대한약학회 1992 약학회지 Vol.36 No.2
A new method for felbinac, which is a potent anti-inflammatory agent, is described. Friedel-Crafts reaction of biphenyl with ethyl alpha-chloro-alpha-(methylthio)acetate(1) afforded ethyl 2-methylthio-2-(4-biphenylyl)acetate(4). Felbinac (7) was synthesized by desulfurization of compound (4) with zinc dust in acetic acid, followed by hydrolysis of the resultant ethyl 2-(4-biphenylyl)acetate(6).