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Synthesis method of cyclic orthoester monomer containing diamino

A synthetic method, diamino technology, applied in the fields of biomedicine and organic chemistry

Inactive Publication Date: 2014-05-21
唐汝培
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  • Abstract
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  • Application Information

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  • Synthesis method of cyclic orthoester monomer containing diamino
  • Synthesis method of cyclic orthoester monomer containing diamino
  • Synthesis method of cyclic orthoester monomer containing diamino

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Embodiment 1

[0020] Preparation of 4,4'-dimethyleneoxy-bis-(2-methoxy-1,3-dioxolane)

[0021] Under the protection of nitrogen, add 10.0g (60.18mmol) diglycerin to a 250mL three-necked flask, add 100mL acetonitrile to dissolve, then add 51.08g (480mmmol), and finally add 260mg p-toluenesulfonic acid under stirring, and react overnight at room temperature. After the crude product was distilled off under reduced pressure to remove the organic solvent, it was dissolved by adding ethyl acetate, washed with 10% sodium carbonate solution, dried over magnesium sulfate, removed the organic solvent by distillation under reduced pressure, and vacuumized to obtain 14.93 g of a colorless oily product with a yield of 85.85%. . 1H NMR (400MHz, CDCl 3 ): 3.32-3.33 (s, 3H, OCH 3 ), 3.51-3.84 (m, 2H, OCH 2 ), 4.07-4.16 (m, 2H, OCH 2 ), 4.28-4.48 (m, 1H, OCHCH 2 ), 5.74-5.78 (t, 1H, OCHO)

[0022] 4,4'-Dimethyleneoxy-bis-[2,2,2-trifluoro-N-(2-methoxy-1,3-dioxolane-4-ethylene)acetamide]

[0023] Add ...

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Abstract

The invention relates to a synthesis method of a cyclic orthoester monomer containing diamino, which belongs to the technical field of biological medicine and organic chemistry. The monomer is 4, 4'-dimethylene oxygen-di-(2-aminoethoxy-2-R-1, 3-dioxolane), and is a novel polyorthodester monomer, wherein R is hydrogen or methyl. The synthesis method of the orthoester monomer comprises the steps that dimeric glycerin is used as a raw material, and reacts with trimethyl orthoester in the presence of an acid catalyst; ester exchange reaction is carried out on an acquired product and 2-trifluoro acetamido ethanol in the presence of a catalyst to acquire a precursor compound of the monomer; and finally, a trifluoroacetyl protective group is removed from the precursor compound in an alkaline solution to acquire the cyclic orthoester monomer containing diamino. According to the synthesis method provided by the invention, the raw material can be easily acquired; the synthesis method is simple and economic, and is suitable for industrialized production; and the monomer is stable at room temperature, and can be used for the preparation and the application development of a novel polyorthodester polymer biomaterial.

Description

technical field [0001] The invention relates to a synthesis method of a diamino-containing cyclic ortho ester monomer, belonging to the technical fields of biomedicine and organic chemistry. Background technique [0002] Polyorthoesters (Polyorthoesters, POE) is an acid-sensitive and biodegradable polymer material. Since it was first synthesized by Jorge Heller and his colleagues in the United States in the 1960s, because of its good surface controllable erosion performance, it has been widely used in drug slowdown. The field of controlled release has developed rapidly. At present, the slow-release preparations of anti-tumor drugs and anti-narcotic antagonists of this excipient are undergoing phase IV clinical trials, and are expected to be approved by the US FDA. [0003] Polyorthoesters have been developed for four generations (Heller, J., et al., Advanced Drug Delivery Reviews, 2002.54(7): p.1015-1039.; Heller, J.and J.Barr, Biomacromolecules, 2004.5(5) : p.1625-1632.),...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D317/34
CPCC07D317/34Y02P20/55
Inventor 唐汝培陶扬洋
Owner 唐汝培
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