Process for producing optically active triazole compounds and method of racemizing optically active triazole compounds
AssigneeDaicel Chemical Industries, Ltd.
InventorsNaoki Kawada, Noritsugu Yamazaki, Takafumi Imoto, Kiyoshi Ikura
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Abstract
A process for the asymmetric synthesis of a compound represented by general formula (II-R) easily at a low cost by using a lipase, and a process for producing a compound to be utilized in the above synthesis. ##STR1##
Claims31
A process for producing a compound having the formula (II-R), said process comprising the steps of
- (a) providing a compound having the formula (II), a compound having the formula R.sub.1 COOR.sub.2, and a microbial lipase;
- and
- (b) enzymatically reacting said compound having the formula (II) with said compound having the formula R.sub.1 COOR.sub.2, in the presence of said microbial lipase, under conditions permitting formation of a compound having the formula (II-R);
- ##STR6## wherein X and Y are either halogen or hydrogen atoms, wherein X and Y may be the same or different atoms;
- wherein the configuration of the asymmetric carbon is R;
- and
- wherein R.sub.1 is a straight or branched C.sub.1 to C.sub.4 alkyl or alkenyl group, and R.sub.2 is a straight or branched C.sub.1 to C.sub.6 alkyl or alkenyl group.
A process for producing a compound having the formula (I-R), said process comprising the steps of
- (a) providing a compound having the formula (II), a compound having the formula R.sub.1 COOR.sub.2, and a microbial lipase;
- and
- (b) enzymatically reacting said compound having the formula (II) with said compound having the formula R.sub.1 COOR.sub.2, in the presence of said microbial lipase, under conditions permitting formation of a compound having the formula (I-R);
- ##STR7## wherein X and Y are halogen or hydrogen atoms;
- wherein X and Y may be the same or different atoms;
- wherein the configuration of the asymmetric carbon is R;
- and
- wherein R.sub.1 is a straight or branched C.sub.1 to C.sub.4 alkyl or alkenyl group, R.sub.2 is a straight or branched C.sub.1 to C.sub.6 alkyl or alkenyl group, and R is COR.sub.1.
A process for producing a compound having the formula (II-R), said process comprising the steps of
- (a) providing a compound having the formula (I) and a microbial lipase;
- and
- (b) hydrolyzing said compound having the formula (I) in the presence of said microbial lipase, under conditions permitting formation of a compound having the formula (II-R);
- ##STR8## wherein X and Y are halogen or hydrogen atoms;
- wherein X and Y may be the same or different atoms;
- wherein the configuration of the asymmetric carbon is R;
- and
- wherein R is COR.sub.1, wherein R.sub.1 is a straight or branched C.sub.1 to C.sub.4 alkyl or alkenyl group.
A process for producing a compound having the formula (I-R), said process comprising the steps of
- (a) providing a compound having the formula (I) and a microbial lipase;
- and
- (b) hydrolyzing said compound having the formula (I) in the presence of said microbial lipase, under conditions permitting formation of a compound having the formula (I-R);
- ##STR9## wherein X and Y are halogen or hydrogen atoms;
- wherein X and Y may be the same or different atoms;
- wherein the configuration of the asymmetric carbon is R;
- and wherein R is COR.sub.1, wherein R.sub.1 is a straight or branched C.sub.1 to C.sub.4 alkyl or alkenyl group.
A process for producing a compound having the formula (II) comprising reducing or eliminating the optical activity of a compound having the formula (I-R) or (I-S) by treatment with a strong acid followed by deacylation;
- ##STR10## wherein X and Y are halogen or hydrogen atoms;
- wherein X and Y may be the same or different atoms;
- and
- wherein R is COR.sub.1, wherein R.sub.1 is a hydrogen atom, or a straight or branched alkyl, alkenyl, aryl or aralkyl groups.
A process for producing a compound having the formula (II) comprising reducing or eliminating the optical activity of a compound having the formula (II-R) or (II-S) by treatment with a strong acid in the presence of an acylating agent followed by deacylation;
- ##STR11## wherein X and Y are halogen or hydrogen atoms;
- wherein X and Y may be the same or different atoms.
Dependencies are inferred from the claim text.