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Sorption of high amount of 1,3-thiazol-5-ylmethyl [(2R,5R)-5-{[(2S)-2-[(methyl{[2- (propan-2-yl)-1,3-thiazol-4-yl]methyl}carbamoyl)amino]-4-(morpholin-4- yl)butanoyl]amino}-1,6-diphenylhexan-2-yl]carbamate on Silica

IP.com Disclosure Number: IPCOM000245970D
Publication Date: 2016-Apr-21
Document File: 1 page(s) / 11K

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Sorption of high amount of 1,3-thiazol-5-ylmethyl [(2R,5R)-5-{[(2S)-2-[(methyl{[2- (propan-2-yl)-1,3-thiazol-4-yl]methyl}carbamoyl)amino]-4-(morpholin-4- yl)butanoyl]amino}-1,6-diphenylhexan-2-yl]carbamate on Silica

    Provided herein is high % (about 65%) of 1,3-thiazol-5-ylmethyl [(2R,5R)-5- {[(2S)-2-[(methyl{[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl}carbamoyl)amino]-4- (morpholin-4-yl)butanoyl]amino}-1,6-diphenylhexan-2-yl]carbamate referred herein as Compound I, on silica, and process for the preparation thereof.

    The starting Compound I may be prepared for example according to WO2010/115000.

Example 1: Preparation of 64% (w/w) Compound I loaded on silica
A 1L reactor was charged with a stock solution of Compound I (40 gr) in Me-THF (98.2 gr, 3V). This was followed by the addition of the silica-based solid carrier Aeroperl 300 (20 g). The mixture was stirred over 1 h and then n-heptane (690 mL, 17V) was added drop-wise at 25°C over a period of 1 h with stirring, resulting in precipitation. The solution was cooled under nitrogen to about 0°C. The resulting slurry was then stirred at the same temperature for another 18 h and filtered. The residues inside the reactor were washed with n-heptane and the combined washings were added over the existing filter cake. The cake was dried at 25°C, under reduced pressure for 24 hours to afford the title composition as a white solid (56.7 g, the assay of Compound I on silica was determined by HPLC).