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US 2016/0355471 A1Published application
Preparation of hydroxy-benzylbenzene derivatives
AssigneeTheracos Sub, LLC
InventorsJacques ROBERGE, Carine VAXELAIRE, Baohu LIU, Ge XU, Jian ZHANG, Xinxing TANG, Baihua XU
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Abstract
Methods for preparing intermediates of SGLT2 inhibitors are provided, including crystalline forms and methods of crystallizing intermediates.
Claims17
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.
3 more elements
A method for preparing a crystalline form of a compound having the structure:
- comprising the steps:
- (a) mixing 2-cyclopropoxyethyl-4-methylbenzenesulfonate and a first solvent that is a polar protic solvent to form a solution;
- and
- (b) adding a second solvent to the solution to provide a mixture, under conditions suitable to form the crystalline form of the compound.
1 more element
A crystalline form of the compound having the structure:
- characterized by an X-ray powder diffraction (XRPD) pattern comprising peaks at 14.3, 21.1, 21.9, degrees 2θ (±0.1 degrees 2θ), wherein said XRPD is made using CuKα1 radiation;
- or
- characterized by a Raman spectra comprising peaks at about 110, 778, 1170, and 1206 cm−1.
Dependencies are inferred from the claim text.