Gamma-cyclodextrin modifier as well as preparation method and use thereof
A technology of cyclodextrin and modification, applied in the field of γ-cyclodextrin modification and its preparation, can solve the problems of low yield of sugammadex sodium preparation process, difficult control of reaction conditions, difficulty of purification, etc., to achieve reaction High efficiency, easy industrial production and low cost
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[0027] A preparation method of γ-cyclodextrin modification, 6-deoxy-6-perhalogenated γ-cyclodextrin and 3-(chlorosulfonyl) propionate are prepared to obtain γ-cyclodextrin modification, preparation route as follows:
[0028]
[0029] 6-Deoxy-6-perhalogenated γ-cyclodextrin is prepared from γ-cyclodextrin with triphenylphosphine and halogen.
[0030] Tetrahydrofuran, N,N-dimethylformamide, N,N-dimethylacetamide and dimethyl sulfoxide were added in the preparation reaction of modified γ-cyclodextrin.
[0031] Alkali is added in the preparation reaction of modified γ-cyclodextrin.
[0032] The alkali is sodium hydroxide, potassium hydroxide, sodium methylate, potassium methylate, sodium amide, sodium hydride, potassium tert-butoxide, n-butyllithium, tert-butyllithium, triethylamine, pyridine, diethylamine, ammonia , Ethylenediamine, tetramethylethylenediamine and diisopropylamine, etc.
[0033] The reaction temperature of the preparation reaction of the γ-cyclodextrin modif...
Embodiment 1
[0042] Example 1: Preparation of 2-carbocarboxyethylsulfone-γ-cyclodextrin
[0043]
[0044] Dissolve 50g of dry 6-deoxy-6-perchloro-γ-cyclodextrin in dry 1L of N,N-dimethylformamide, add 22mL of triethylamine and cool down to -30°C, slowly drop After methyl 3-(chlorosulfonyl)propionate, control the temperature to 0°C and react for 2 hours, then slowly add the solution into the reaction liquid, then slowly add the reaction liquid into 1L of drinking water, a large amount of solids are precipitated, suction filtered, and 10 mL of cold water The filter cake was washed with N,N-dimethylformamide to obtain 55 g of off-white solid with a yield of 110%.
[0045] MS (m / z): 2393.35 [M+Na] + . 1 H-NMR (d6-DMSO): δ5.90-5.91 (16H, m), δ4.99-5.01 (8H, m), δ3.55-3.66 (32H, m), δ3.25-3.41 (16H, m), δ3.04-3.11 (8H, m), δ2.74-2.80 (24H, m), δ2.57-2.60 (16H, m).
Embodiment 2
[0046] Example 2: Preparation of 2-carboethoxyethylsulfone-γ-cyclodextrin
[0047]
[0048] Dissolve 25g of dry 6-deoxy-6-perbromo-γ-cyclodextrin in dry 500mL of N,N-dimethylacetamide, add 10mL of pyridine and cool down to -10°C, slowly add 3- After ethyl (chlorosulfonyl)propionate, control the temperature to 10°C and react for 1.5h, slowly add the solution into the reaction solution, slowly add the reaction solution into 500mL of drinking water, a large amount of solid is precipitated, suction filtered, 10mL of cold The filter cake was washed with N,N-dimethylacetamide to obtain 28 g of an off-white solid with a yield of 112%.
[0049] MS(m / z): 2483.57[M+H] + . 1 H-NMR (d6-DMSO): δ5.91-5.93 (16H, m), δ4.99-5.04 (8H, m), δ3.76-4.03 (24H, m), δ3.24-3.43 (16H, m), δ3.09-3.13 (8H, m), δ2.75-2.83 (24H, m), δ2.56-2.60 (16H, m), δ1.27-1.33 (24H, m).
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