Process for producing alpha-sulfophenylacetic acid derivatives
AssigneeTakeda Chemical Industries, Ltd.
InventorsKeiichi Sugimoto, Koji Nishijima, Hiroshi Akimoto, Tadashi Hanaoka, Nobuharu Kakeya
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Abstract
.alpha.-Sulfophenylacetic acid derivatives of the general formula: ##STR1## (wherein R is a substituted or unsubstituted primary alcohol, cyclic alcohol or phenol compound residue), which are of value as intermediates of antibacterial agents, are selectively produced in a high yield by bringing a diester compound of the general formula: ##STR2## (wherein R has the same meaning as defined above) into contact with a strong acid.
Claims11
A method for producing .alpha.-sulfophenylacetic acid derivatives of the formula:
- ##STR95## in which R is isobutyl or --CH.sub.2 R' in which R' is a branched alkyl group of 4 to 14 carbon atoms, which comprises reacting .alpha.-chlorosulfonylphenylacetyl chloride with tertiary butanol at a temperature of -30.degree. C. to 30.degree. C. to produce an .alpha.-chlorosulfonylphenylacetic acid tertiary butyl ester;
- reacting the .alpha.-chlorosulfonylphenylacetic acid tertiary butyl ester with an alcohol of the formula:
- R--OH
- in which R has the same meaning as defined above at a temperature of -20.degree. C. to 40.degree. C. to produce a diester compound of the formula:
- ##STR96## wherein R has the same meaning as defined above;
- and then bringing the diester compound into contact with a mineral acid in the absence of a solvent or in the presence of a solvent selected from the group consisting of dichloromethane, chloroform, carbon tetrachloride, benzene and toluene at a temperature of -30.degree. C. to 50.degree. C.
A method for producing a .alpha.-sulfophenylacetic acid derivatives of the formula:
- ##STR97## in which R is isobutyl or --CH.sub.2 R' wherein R' is a branched alkyl of 4 to 14 carbon atoms, which comprises bringing a diester compound of the formula:
- ##STR98## wherein R has the same meaning as defined above into contact with a mineral acid in the absence of a solvent or in the presence of a solvent selected from the group consisting of dichloromethane, chloroform, carbon tetrachloride, benzene and toluene at a temperature of -30.degree. C. to 50.degree. C.
Dependencies are inferred from the claim text.