Diisopropylethylamine → HCID 67342269, compound

Participants

Reaction Conditions

Reaction Steps

50 mg (0.12 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrochloride and 44 mg (0.13 mmol) of (S)-2-tert-butoxycarbonylamino-4-(tert-butyldimethylsilanyloxy)butyric acid (preparation analogous to Tetrahedron, 2005, vol. 61, #43 p. 10277-10284) were dissolved in 1 ml of DCM together with 50 μl (0.29 mmol) of N-ethyldiisopropylamine and stirred at 0° C. for 5 min. 73 mg (0.14 mmol) of benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate and 50 μl (0.29 mmol) of ethyldiisopropylamine were then added. The mixture was stirred further at 0° C. for 1 h, diluted with EA and washed by shaking with water and a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution. The organic phase was dried over sodium sulfate, filtered and evaporated. A 1.25 M HCl solution in methanol was then added to the residue, and the mixture was stirred for 1 h. The methanolic solution was evaporated, and the product was purified by means of preparative HPLC. The product is in the form of the hydrochloride.

Provenance & Evidence