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Preparation method of sulfamate

A technology of aminosulfonyl and alkyl, applied in the synthesis of drug molecules, in the field of efficient preparation of sulfamate compounds, can solve problems such as high toxicity and poor functional group compatibility

Pending Publication Date: 2022-05-13
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this reagent has greater toxicity, and the toxicity comes from the decomposition product pentachlorophenol, and the rat oral acute toxicity test LD50=50mg / kg
In addition, its functional group compatibility is poor, and the preparation still needs to use an excessive amount of H 2 NSO 2 Cl

Method used

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  • Preparation method of sulfamate
  • Preparation method of sulfamate
  • Preparation method of sulfamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Example 1: Preparation of sulfamoylating reagent D1.

[0093]

[0094] Under the condition of nitrogen protection, tert-butanol (44mmol, 3260mg) was added to a 250mL reaction flask, 60mL of dry toluene was cooled to 0°C in an ice bath, chlorosulfonyl isocyanate (40mmol, 5660mg) was added dropwise, and stirred at 0°C for one Hours, after adding pyridine (88mmol, 6960mg) dropwise, the mixture was raised to room temperature and stirred for 3 hours, a white solid precipitated out. Quickly suction-filtered, washed once with diethyl ether, the solid was transferred to a 100mL flask, and vacuum-dried for 20 minutes to obtain the white solid product D1 without purification, with a yield of 92%. 1 H NMR (400MHz, CDCl3) δ8.92 (dd, J = 6.6, 1.5Hz, 4H), 8.48 (tt, J = 7.8, 1.6Hz, 2H), 8.01 (dd, J = 7.8, 6.6Hz, 4H) ,7.40(s,1H),1.41(s,9H).

Embodiment 2

[0095] Example 2: Preparation of sulfamoylating reagent D2.

[0096]

[0097] Under the condition of nitrogen protection, tert-butanol (44mmol, 3260mg) was added to a 250mL reaction flask, 60mL of dry toluene was cooled to 0°C in an ice bath, chlorosulfonyl isocyanate (40mmol, 5660mg) was added dropwise, and stirred at 0°C for one After 4-picoline (88mmol, 8195mg) was added dropwise, the mixture was raised to room temperature and stirred for 3 hours, and a white solid precipitated out. Suction filtration was rapid, washed once with ether, the solid was transferred to a 100 mL flask, and dried in vacuum for 20 minutes to obtain the white solid product D2 without purification, with a yield of 90%. 1 H NMR (400MHz, CDCl 3 )δ8.71(d, J=6.6Hz, 4H), 7.73(d, J=6.2Hz, 4H), 2.65(s, 6H), 1.41(s, 9H).

Embodiment 3

[0098] Example 3: Preparation of sulfamoylating reagent D3.

[0099]

[0100] Under nitrogen protection, add 9-fluorenemethanol (44mmol, 8634mg) and 60mL of dry toluene to a 250mL reaction flask, cool to 0°C in an ice bath, add chlorosulfonyl isocyanate (40mmol, 5660mg) dropwise, and stir at 0°C After one hour, pyridine (88 mmol, 6960 mg) was added dropwise, and the mixture was raised to room temperature and stirred for 3 hours, and a white solid precipitated out. Suction filtration was rapid, washed once with ether, the solid was transferred to a 100mL flask, and dried in vacuum for 20 minutes to obtain the white solid product D1, which did not need to be purified, and the yield was 85%. 1 H NMR (400MHz, CDCl 3 )δ8.85(d,J=5.3Hz,4H),8.39(t,J=7.8Hz,2H),7.92(dd,J=7.5,6.7Hz,4H),7.76–7.66(m,2H), 7.64–7.53(m,2H),7.35(t,J=7.5Hz,2H),7.26(t,J=7.3Hz,2H),4.40–4.10(m,3H).

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Abstract

The invention relates to a preparation method of sulfamate. Specifically, the invention discloses an amino sulfonylation reagent which has the advantages of low cost, easiness in obtaining, good solubility, high stability and the like. By using the reagent, amino sulfonylation modification of hydroxyl can be realized with high selectivity, the reaction condition is mild, the operation is simple, and the amplification can be realized. The obtained product has the advantages of high yield, few byproducts, high purity and the like.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to the efficient preparation of sulfamate compounds and their application in the synthesis of drug molecules. Background technique [0002] Sulfamate has unique chemical and biological properties, and has important applications in organic chemistry, medicinal chemistry and other fields. In the synthesis reaction, sulfamate is not only the precursor of the cross-coupling reaction (J.Am.Chem.Soc.2009,131,17748), but also the amino donor in the hydrocarbon activation system (Org.Lett.2020,22,168 ). On the other hand, as a pharmacophore, sulfamate is an isosteric analog of sulfonate and phosphate, which is electrically neutral in a physiological environment, and its unique interaction mode makes it often used as an adjustment agent in drug molecules. Important group for bioactivity and bioavailability (J. Med. Chem. 2003, 46, 2197). [0003] So far, the direc...

Claims

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Application Information

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IPC IPC(8): C07D213/89C07D213/127C07D213/16C07D213/18C07C303/34C07C307/02C07J41/00C07D213/40C07D233/94C07D311/32C07D487/04
CPCC07D213/89C07D213/127C07D213/16C07D213/18C07C303/34C07C307/02C07J41/0055C07J41/0038C07D213/40C07D233/94C07D311/32C07D487/04C07C2601/16C07B2200/07
Inventor 王东宇张翱
Owner SHANGHAI JIAO TONG UNIV
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