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Preparation of (1S,2S,3S,5Z,7E)-2-(3-Hydroxypropoxy)-9,10-secocholesta-5,7,10-triene-1,3,25-triolin Ethyl Acetate Disclosure Number: IPCOM000241932D
Publication Date: 2015-Jun-09
Document File: 1 page(s) / 202K

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Preparation of (1S,2S,3S,5Z,7E)-2-(3-Hydroxypropoxy)-9,10-secocholesta-5,7,10-

triene-1,3,25-triolin Ethyl Acetate

    Provided herein is a process for purification of crude (1S,2S,3S,5Z,7E)-2-(3- Hydroxypropoxy)-9,10-secocholesta-5,7,10-triene-1,3,25-triol (referred to as Compound 1) by crystallization. The process is described in Example 1.

Example 1:

Compound 1 (crude, 172 mg) prepared according to a procedure, known from the literature,

(Heterocycles, 2006, 70, 295), was mixed with ethyl acetate (0.6 mL) at 25 ºC. The suspension was

stirred at 25 ºC for 2h and cooled to -20 ºC. The crystals were separated by filtration, washed with

ethyl acetate and dried overnight at 25 ºC to give white crystals (96 mg) with HPLC purity 95.46 %.

The obtained solid was analyzed by XRPD to provide a crystalline form as shown in Figure 1. Figure 1: XRPD of a crystalline form of Compound I

Main peaks:5.2, 10.0, 11.9, 14.0, 15.8, 17.2, 17.9, 18.8, 20.4, and 22.8 degrees 2-theta ± 0.2 degrees 2-theta.

XRPD method:

The sample was adjusted in a 0.7 mm capillary (Glas 50, Hilgenberg). The sample was measured by the Empyrean (PANalytical) instrument with focusing mirror, detector PIXcel 3D Cu lamp (Cu Kalpha1,2) from 4° to 30° 2theta, 20 min., with open Soller slits.

According to Figure 1, the crystalline form of Compound I is characterized by

XRPD peaks at: 5.2, 10.0, 11.9, 14.0, 15.8, 17.2, 17.9, 18.8, 20.4, and 22.8 ± 0.2 degrees 2-theta.