• 대한화학회지
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• 제23권3호
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• pp.175-179
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• 1979

Phthalimido기와 2,2,2-trichloroethyl기는 acetic acid와 같은 산성용매에서 zine dust에 의하여 각각 3-hydroxyphthalimidino기로 환원 되거나 혹은 환원분해된다. 그러나 THF-pH 4.5 buffer 혼합용매를 사용하므로써, free carboxylic acid가 존재하지 않는 경우, phthalimido는 환원시키지 않고 2,2,2-trichloroethyl기만을 선택적으로 환원분해시킬 수 있음을 발견하였다. 따라서 $2,2,2-trichloroethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-{\beta}-D-glucopyranose$ (1)를 THF-pH 4.5 butter 혼합용매에서 zinc dust와 반응시키면, 2,2,2-trichloroethyl 기만이 선택적으로 환원분해된 $3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-{\beta}-D-glucopyranose$ (5)를 좋은 수득율로 얻을 수 있었다.

• 약학회지
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• 제35권2호
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• pp.131-134
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• 1991

A new method for the synthesis of butibufen, which is a non steroidal anti-iriflammatory 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 Etl. 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).

• 약학회지
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• 제40권6호
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• pp.640-645
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• 1996

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 du st-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.

• 약학회지
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• 제33권4호
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• pp.237-240
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• 1989

A new synthetic method for tiaprofenic acid, which is a potent anti-inflammatory agent, was described. Friedel-Crafts reaction of thiophene with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)$ acetate (1) gave ethyl ${\alpha}-methylthio-2-thiopheneacetate$ (3). Ethyl ${\alpha}-methyl-2-thiopheneacetate$ (5) was prepared by treatment of (3) with NaH and MeI, followed by desulfurization with zinc dust-acetic acid of the resultant ethyl ${\alpha}-methyl-{\alpha}-methylthio-2-thiopheneacetate$ (4). Tiaprofenic acid (7) could be easily synthesized by benzoylation of (5) and hydrolysis of the resultant ethyl $5-benzoyl-{\alpha}-methyl-2-thiopheneacetate$ (6).

• 약학회지
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• 제34권3호
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• pp.212-214
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• 1990

A new synthetic method for bufexamac, which is a potent anti-inflammatory agent, was described. Friedel-Crafts reaction of butoxybenzene (2) with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate$ (1) gave ethyl 2-methylthio-2-(p-butoxyphenyl) acetate (3). Ethyl 2-(p-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.

• 약학회지
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• 제41권4호
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• pp.480-483
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• 1997

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.

• 약학회지
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• 제36권4호
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• pp.341-344
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• 1992

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).

• 약학회지
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• 제35권2호
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• pp.119-122
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• 1991

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-isobutylpheny) acetate (4). Ethyl 2-methylthio-2-(4-isobutylphenyl) propionate (5) is obtained from methylation of the compound (4) with NaH and Mel. lbuproxam (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 H$_{2}$NOH-HCI.

• 약학회지
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• 제32권5호
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• pp.340-342
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• 1988

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 $SnCl_4$. 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.

• 약학회지
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• 제36권2호
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• pp.137-139
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• 1992

A new method for xenbucin, which is a antihypercholesteremic agent, is described. Friedel-Crafts reaction of biphenyl with ethyl ${\alpha}-chloro-{\alpha}-(methylthio)acetate(1)$ afforded ethyl 2-methylthio-2-(4-biphenylyl)acetate(2). Ethyl 2-(4-biphenylyl)butyrate(4) was obtained by ethylation of (2) with NaH and $C_2H_5I$, followed by desulfurization of the resultant ethyl 2-methylthio-2-(4-biphenylyl)butyrate(3) with zinc dust in acetic acid. Xenbucin was synthesized by hydrolysis of (4).