Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1999-01-27
1999-11-09
Ambrose, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
558131, 558169, C07F 909, C07F 910, C07F 96574
Patent
active
059817860
DESCRIPTION:
BRIEF SUMMARY
FIELD OF ART
The present invention relates to a process for producing a (meth)acrylate derivative having a (meth)acrylate group, and either a dioxaphosphorane group or a dioxaphosphorinane group.
BACKGROUND OF ART
Phospholipids are known to be a component of a biomembrane. Phosphatidylcholine, one of phospholipids, is a glycerin ester of a long chain alkylcarboxylic acid having a phosphorylcholine group in polar part thereof.
Recently, some attempts have been made to synthesize a phospholipid-like compound having the phosphorylcholine group. For example, there is known a method for producing the objective phosphorylcholine derivative by reacting 2-chloro-2-oxo-1,3,2-dioxaphosphorane (sometimes referred to hereinbelow as "COP") with a compound having a hydroxyl group in the presence of a tertiary amine such as triethylamine, which acts as hydrogen chloride catcher, to produce 2-oxo-1,3,2-dioxaphosphorane derivative; and then reacting the resulting derivative with trimethylamine (Bull. Soc. Chim. Fr., p667-671, 1974, C. R. Acad. Sc. Paris, t.283 Serie C, p229-231, 1976, Zh. Org. Khim. 16(1), p31-33, 1980, C. R. Acad. Sc. Paris, t.275 Serie C, p1125-1127, (1972)).
There is also known a 2-((meth)acryloyloxy)alkyl-2-(trimethylammonium)ethyl phosphate (sometimes referred to hereinbelow as "(M)APC") having the phosphorylcholine group and a (meth)acryloyl group introduced thereto as a polymerizable group. Methods for producing this "(M)APC" and 2-(2-oxo-1,3,2-dioxyaphosphoryl)alkyl (meth)acrylate, an intermediate product of this "(M)APC" (sometimes referred to hereinbelow as "OP(M)A"), have also been proposed.
For example, it is known that the intermediate product "OPMA" may be produced by reacting 2-hydroxyethyl methacrylate with "COP" in the presence of a tertiary amine, and removing the by-product, that is, hydrochloride of the tertiary amine. It is also known that "MAPC" may be produced by reacting the obtained "OPMA" with a tertiary amine such as trimethylamine (JP-B-2-49316, and WO95/14702 specification). However, in these production methods, it is difficult to sufficiently remove the by-product due to the tertiary amine, which has been used as the hydrogen chloride catcher. In addition, the reaction liquid and the objective "(M)APC" tend to be colored in pale yellow or dark brown. Further, the reaction rate is not sufficiently fast.
Then, it has been proposed to perform reaction under reduced pressure in the absence of a tertiary amine (JP-A-8-239394). However, in this method, hydrogen chloride gas is generated as a result of the reaction under the reduced pressure. It takes a long time to remove the gas. Further the reaction results in low reaction ratio.
It has also been proposed to produce "(M)APC" by reacting 2-hydroxyethyl methacrylate with "COP" using specific acetonitrile in the presence of triethylamine, and then opening the ring by reaction with trimethylamine, and optionally re-crystallizing the product from dry acetonitrile (JP-A-9-505578). However, the coloring of the reaction liquid and the product also occurs in this method. Thus, for producing, e.g., a contact lens by polymerizing the obtained "(M)APC", it is required to perform the step of removing the coloring substance from "(M)APC", such as absorption by activated charcoal, re-crystallization or column chromatography, and the production step cannot therefore be simplified.
DISCLOSURE OF THE INVENTION
The object of the present invention is to provide a process for producing a (meth)acrylate derivative with fast reaction rate, and high yield of the product in high purity.
Another object of the present invention is to provide a process for producing a (meth)acrylate derivative in which coloring of the reaction liquid and product is lowered, and the purification steps can be simplified.
The present inventors made extensive studies for solving the above problems, and found out that it is possible to suppress the generation of by-products including coloring substance and to obtain the objective product at fast reaction rate, by employmen
REFERENCES:
patent: 4041012 (1977-08-01), Albright et al.
patent: 5741923 (1998-04-01), Driver et al.
Hayashi Akio
Kitano Shigeru
Matsuyama Kazuo
Murata Yoshishige
Nakamoto Ken-ichiro
Ambrose Michael G.
NOF Corporation
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