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US 10,093,616 B2Granted
Preparation of hydroxy-benzylbenzene derivatives
AssigneeTheracos Sub, LLC
InventorsJacques Roberge, Carine Vaxelaire, Baohu Liu, Ge Xu, Jian Zhang, Xinxing Tang, Baihua Xu
Life of this patent
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Abstract
Methods for preparing intermediates of SGLT2 inhibitors are provided, including crystalline forms and methods of crystallizing intermediates.
Claims15
A method of preparing a compound of Formula III:
- the method comprising:
- (a) forming a first reaction mixture comprising Mg and a compound having the structure:
- in tetrahydrofuran solvent, under conditions suitable to form an intermediate compound having the structure:
- (b) contacting the first reaction mixture with water and 2-methyl-tetrahydrofuran such that the intermediate of step (a) is substantially dissolved in the 2-methyl-tetrahydrofuran;
- and
- (c) forming a second reaction mixture comprising 4-methylbenzene-1-sulfonyl chloride (Tosyl-Cl) and the 2-methyl-tetrahydrofuran of step (b) containing the intermediate of step (a), under conditions suitable to form the compound of Formula III,
- wherein the 2-methyl-tetrahydrofuran containing the intermediate of step (a) is used in step (c) without removing the 2-methyl-tetrahydrofuran to form a concentrated intermediate.
4 more elements
The method of 1, wherein at least about 75% of the intermediate of step (a) is dissolved in the 2-methyl-tetrahydrofuran in step (b).
The method of 1, wherein at least about 90% of the intermediate of step (a) is dissolved in the 2-methyl-tetrahydrofuran in step (b).
Dependencies are inferred from the claim text.