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Method for preparing 2, 3, 4, 6-tetra-O-trimethylsilyl-D-glucolactone by using continuous flow micro-channel reactor

A technology of gluconolactone and microchannel reactor, which is applied in chemical instruments and methods, compounds of group 4/14 elements of the periodic table, organic chemistry, etc., and can solve the problems of low reaction efficiency, complex operation, and non-continuous production, etc. question

Pending Publication Date: 2021-09-10
JIANGSU ALPHA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] But 1,5-gluconolactone reacts with trimethylsilyl protecting group to prepare 2,3,4,6-tetra-O-trimethylsilyl-D-gluconic acid still has big problems, existing Most of the chlorination reaction devices are batch reaction devices, which have problems such as low reaction efficiency, long time, high energy consumption, low product conversion rate, and many impurities.
In addition, it cannot be produced continuously, and the production capacity is limited, which reduces the market competitiveness
[0014] The existing 2,3,4,6-tetra-O-trimethylsilyl-D-gluconic acid production processes are all batch-type, adopting the method of tank reaction-separation-rectification purification, and separation reaction after single-pot reaction Long time, complex operation and many by-product impurities; there are many technical problems to be solved in the production process and control of reaction conditions, 2,3,4,6-tetra-O-trimethylsilyl-D-gluconic acid continuous Chemical production has not been reported

Method used

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  • Method for preparing 2, 3, 4, 6-tetra-O-trimethylsilyl-D-glucolactone by using continuous flow micro-channel reactor
  • Method for preparing 2, 3, 4, 6-tetra-O-trimethylsilyl-D-glucolactone by using continuous flow micro-channel reactor
  • Method for preparing 2, 3, 4, 6-tetra-O-trimethylsilyl-D-glucolactone by using continuous flow micro-channel reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] combine Figure 1-2 As shown, using microchannel reactor 1 (see figure 1 ), the preparation of 2,3,4,6-tetra-O-trimethylsilyl-D-gluconic acid by continuous flow microchannel reaction using hexamethyldisilazane to protect the hydroxyl group of 1,5-gluconolactone The method of lactone is carried out according to the following steps:

[0049] 1) Add 100g of 1,5-gluconolactone into 500ml of chloroform, stir and cool down to 5-10°C, keep it warm to obtain A test solution, about 600ml.

[0050] 2) Dissolve 2.8g of iodine in 10ml of chloroform to obtain B test solution, about 11ml.

[0051] 3) Add test solution B to test solution A dropwise at 5-10°C, and mix to obtain test solution C, about 610ml.

[0052]4) Dilute 361g of hexamethyldisilazane (4 equivalents) with 800ml of chloroform to obtain D test solution, about 1000ml.

[0053] 5) Stir 1000ml of chloroform at the outlet of the microchannel reactor, and control the temperature at 30-35°C.

[0054] 6) Configure 10 g o...

Embodiment 2

[0061] In Example 1, 271g of hexamethyldisilazane (3 equivalents) was added instead; other process conditions remained unchanged.

[0062] Subsequent operations such as dilution, quenching, pickling, pH adjustment, concentration, and distillation yielded 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone with a product yield of 80%. 98% purity.

Embodiment 3

[0064] In Example 1, 452g hexamethyldisilazane (5 equivalents) was added instead; other process conditions were unchanged.

[0065] Subsequent operations such as dilution, quenching, pickling, pH adjustment, concentration, and distillation yielded 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone with a product yield of 85%. 98.8% purity.

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Abstract

The invention relates to the technical field of synthesis of medical intermediates, in particular to a method for preparing 2, 3, 4, 6-tetra-O-trimethylsilyl-D-glucolactone by using a continuous flow micro-channel reactor. In a continuous flow micro-channel reactor, 1, 5-glucolactone and hexamethyldisilazane are used as raw materials, iodine is used as a catalyst, and a target product is prepared within the reaction time of dozens of seconds. The method is simple and safe to operate, high in yield, short in reaction time and capable of realizing continuous production, the product yield is 80% or above, and the purity reaches 98% or above.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, and specifically relates to a continuous flow production method for preparing 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone. Background technique [0002] Diabetes is a group of metabolic diseases characterized by hyperglycemia. Hyperglycemia is caused by defective insulin secretion or impaired biological action, or both. The long-term high blood sugar in diabetes leads to chronic damage and dysfunction of various tissues, especially the eyes, kidneys, heart, blood vessels, and nerves. [0003] Empagliflozin is a selective type 2 sodium glucose cotransporter (SGLT2) inhibitor developed by Boehringer Ingelheim, Germany, and was approved by the FDA in August 2014 for the treatment of type 2 diabetes. SGLT2 inhibitors mainly inhibit the expression of SGLT2 in the kidney, reduce the reabsorption of glucose by the kidney, increase the excretion of glucose in the u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18
CPCC07F7/188
Inventor 陈本顺石利平李大伟徐春涛王龙张维冰钱若灿杨武林江涛
Owner JIANGSU ALPHA PHARM CO LTD
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