2,2,2-Trifluoroethanol → HCID 86753152, compound

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Reaction Steps

A solution of 0.47g of benzyl 5-[(Nα -benzylbxycarbonyl-NG -(2,2,5,7,8-pentamethylchroman-6-sulphonyl)-L-arginyl-glycyl-4-O-tert-butyl-L-aspartyl-L-valyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 25 ml of trifluoroethanol was stirred under hydrogen for 2 hours in the presence of palladium/charcoal (10%). Thereafter, the catalyst was filtered off and the filtrate was brought to dryness, The residue was taken up in 20 ml of dimethylformamide together with 0.34 ml of diisopropylethylamine. The solution obtained was added dropwise within 20 minutes to a solution of 0.66 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate in 50 ml of dimethylformamide, whereupon the mixture was stirred at room temperature for 1 hour. Subsequently, the majority of the solvent was removed in a vacuum, whereupon the concentrate obtained was poured into dilute sodium bicarbonate solution. The resulting precipitate was filtered off, washed with water and dried. This crude product was dissolved in a mixture of 20 ml of trifluoroacetic acid, 0.5 ml of water and 0.2 ml of phenol. The solution was left to stand at room temperature for 1 hour and then concentrated. The residue remaining was digested with ether and lyophilized from glacial acetic acid. After purification by HPLC (C-18 phase; gradient: water/ethanol with 0.1% trifluoroacetic acid) 75 mg of 4,5-cyclo-[acetyl-L-arginyl-glycyl-L-aspartyl-L-valyl-aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene trifluoroacetate(4,5-cyclo-[acetyl-SEQ ID NO:2-aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene trifluoroacetate) were obtained; IR 3364, 2965, 2841, 1664, 1577 and 1497 cm-1 ; MS: 767 (M+H)+.

Provenance & Evidence