Crystals of intermediate for benzindene prostaglandins and methods for preparation thereof
A crystal, crystallization technology, applied in chemical instruments and methods, organic chemistry methods, purification/separation/stabilization of organic compounds, etc. Unsatisfactory quality, etc.
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[0078] X-Ray Powder Diffraction (XRPD) Analysis: XRPD patterns were collected on a Bruker D2 PHASER diffractometer with fixed divergence slit and ID LYNXEYE detector. The sample (approximately 100 mg) was placed flat on the sample holder. Use CuK α Radiation The as-prepared samples were analyzed at a power of 10 mA and 30 kV over a 2θ range of 2° to 50° with a step size of 0.02° and a step time of 1 s. Removal of CuK by Diverging Beam Nickel Filter β radiation.
[0079] Differential Scanning Calorimetry (DSC) Analysis: DSC thermal analysis patterns were collected on a TA DISCOVERY DSC25 instrument. Samples (approximately 5 mg) were weighed into aluminum pans with crimped closed aluminum lids. The prepared samples were analyzed from 10°C to 100°C at a scan rate of 10°C / min under nitrogen flow (approximately 50ml / min). The melting temperature and heat of fusion were calibrated by indium (In) before measurement.
[0080] Fourier transform infrared (FTIR) analysis: FTIR spec...
example 1
[0082] Preparation of Crude Cetyl Treprostinil Preparation of Crude Compound (I)
[0083] (1R,2R,3aS,9aS)-1-((S)-3-Hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2 , 5-diol (20.00g, 0.06mol) was dissolved in dry acetone (200ml) with potassium carbonate (20.70g, 0.15mol), chloroacetonitrile (6.40ml, 0.10mol) and tetrabutyl bromide (3.20g, 0.01mmol )deal with. The mixture was heated at 30°C overnight. Subsequently, the reaction mixture was filtered through a pad of celite. The filtrate was evaporated under vacuum. The crude product was purified by silica gel chromatography using a mixture of hexane and ethyl acetate as eluent gradient to obtain 16.4 g of a viscous liquid (crude compound (I)).
example 2
[0085] Preparation of Crystalline Form I of Compound (I)
[0086] Crude compound (I) (1.00 g from Example 1) and isopropyl ether (15 ml) were heated to 40°C for dissolution and then cooled to room temperature. n-Heptane (17ml) was slowly added dropwise and the mixture was stirred in an ice-water bath for 20 hours until solid precipitation occurred. Subsequently, the resulting suspension was filtered and rinsed, and then dried under high vacuum at room temperature for 24 hours, yielding 0.90 g of crystalline Form I of compound (I). XRPD, DSC and FTIR results with figure 1 , figure 2 and image 3 same as shown in .
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