Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method for preparing marine alkaloid baculiferin-1 intermediate

A technology for intermediates and substances is applied in the field of preparation of natural marine alkaloids BaculiferinL intermediates, and can solve the problems of using expensive catalysts, low yield, increased cost and the like

Active Publication Date: 2020-06-23
ZHEJIANG UNIV OF TECH
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the use of expensive catalysts in this process condition, the cost increases, and the yield is low, it is difficult to realize the scale-up production of pilot scale

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method for preparing marine alkaloid baculiferin-1 intermediate
  • A kind of synthetic method for preparing marine alkaloid baculiferin-1 intermediate
  • A kind of synthetic method for preparing marine alkaloid baculiferin-1 intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1, the synthesis of the Baculiferin L intermediate shown in formula (a):

[0053]

[0054] (1) Put nitrilotriacetic acid (10g, 52.3mmol) in 50mL of methanol solvent, stir at room temperature, add 2.78ml of concentrated sulfuric acid solution, heat up to 65°C after the addition, reflux for 18h, and TLC detects that the reaction is complete. The methanol in the reaction solution was concentrated under reduced pressure, the residue was dissolved in dichloromethane, washed successively with saturated sodium bicarbonate solution (50 mL×2) and saturated sodium chloride (50 mL×2), and the organic layer was dried over anhydrous sodium sulfate , filtered with suction, and the filtrate was concentrated to obtain the compound represented by formula (I), with a yield of 81.14%.

[0055] (2) Compound (2.5g, 10.7mmol) shown in formula (I) and dimethyl oxalate (1.266g, 10.7mmol) were dissolved in sodium methylate solution (from sodium block (1.331g, 0.058mol) and methano...

Embodiment 2

[0078] Embodiment 2, the synthesis of the Baculiferin-L intermediate shown in formula (b):

[0079]

[0080] (1) Put benzyliminodiacetic acid (11.7g, 52.4mmol) in 50mL of methanol solvent, stir at room temperature, add 2.79mL of concentrated sulfuric acid solution, heat up to 65°C after the addition, reflux for 18h, and detect the reaction by TLC After completion, the methanol in the reaction solution was concentrated under reduced pressure, the residue was dissolved in dichloromethane, washed with saturated sodium bicarbonate solution (50mL×2) and saturated sodium chloride (50mL×2) successively, and the organic layer was washed with anhydrous Dry over sodium sulfate, filter with suction, and concentrate the filtrate to obtain the compound shown in formula (I);

[0081] (2) The compound represented by formula (I) (4.3g, 17.1mmol) and dimethyl oxalate (2.01g, 17.1mmol) were dissolved in sodium methoxide solution (from sodium block (1.96g, 0.085mol) and methanol (25mL ), aft...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesis method for preparing a marine alkaloid Baculiferin-L intermediate. According to the method, a novel synthesis route suitable for the Baculiferin-L intermediate is designed, which is started from a raw material, substituted aminodiacetic acid, and successively includes an esterification reaction, a Hinsberg reaction, a Pd-catalyzed Suzuki-Miyaura reaction, a hydrolysis reaction, a decarboxylation reaction, a substitution reaction, a reduction reaction and a cyclization reaction and the like. The route reduces usage of expensive catalysts and is greatly increased in reaction yield, so that the method can be used for enlarged production. The synthesis method uses simple and easy-to-obtained raw materials, is carried out under gentle conditions and with low-pollution reagents, is high in yield, has good stability, is low in cost and can be used for pilot scale-up.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and relates to a method for preparing a natural marine alkaloid Baculiferin L intermediate. Background technique [0002] In 2010, Chinese marine research experts used biotechnology to isolate Baculiferin L and other snail-like compounds from the South China Sea sponge Iotrochota Baculifera for the first time. It is reported that this type of compound has strong anti-HIV-1 type targeting activity (Fan G, Li Z, Shen S, et al.Bioorganic&medicinalchemistry, 2010,18(15):5466-5474.), has a high research and development potential value. Since the current way to obtain Baculiferin L is mainly biological extraction, and the extraction cost is high and the extraction utilization rate is low, the large-scale preparation technology has become a technical difficulty for further in-depth research. Scholars at Peking University reported a total synthesis route for Baculiferin L for the first time. P...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/80
Inventor 夏春年孟祥伟邓夏萌沈海伟单伟光王建伟
Owner ZHEJIANG UNIV OF TECH