Process for producing (dioxolenon-4-yl)methyl ester derivative

Details Process for producing (dioxolenon-4-yl)methyl ester derivative Process for producing (dioxolenon-4-yl)methyl ester derivative

2006-05-09

2006-05-09

Dentz, Bernard (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Esterification of the 3-position -cx- group, wherein the x's...

C205S215000, C205S301000, C205S302000, C205S347000

Reexamination Certificate

active

07041820

ABSTRACT:
There is provided a method by which various compounds (1) having a carboxyl group in the molecule have the carboxyl group converted to a (dioxolenon-4-yl)methyl ester at low cost, in a simple way and at high yield.The process for producing compounds of formula (3) according to the reaction scheme shown below comprises reacting carboxylic acids of formula (1) with 4-chloromethyldioxolenone compounds of formula (2) in a solvent in the presence of both a phase transfer catalyst and a metal iodide:[where Q represents an organic group, M represents a hydrogen atom, an alkali metal, an alkaline earth metal or a transition metal, R1and R2represent a hydrogen atom, an optionally substituted (C1-6alkyl group or phenyl group)].

REFERENCES:
patent: 6-192270 (1994-07-01), None
Yeh et al, J. of the Chinese Chemical Soc., vol. 38, p. 221-230 (1991).
Weber et al, Phase Transfer Catalysis in Organic Chemistry, Springer-Verlag, Berlin, p. 1-15 and 85-95 (1977).
Sakamoto et al. Studies on prodrugs. VI. Preparation and Characterization of . . . Esters of Mecillinam, Chem. Pharm. Bull., vol. 35, No. 2, pp. 642-646 (1987).
The Chemical Society of Japan, 4th Edit. Jikken Kagaku Koza 27, Seibutsu Yuki, Maruzen Co. Ltd. p. 251-253 (1991) and English Translation.
Tabuse and Nishitani (translators), “Sokan idou shokubai”, 1st ed. (1978), Kagaku Dojin Publishing Co., p. 1-14 and 99-111) and English language Counterpart.

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