Diisopropylethylamine → HCID 86670471, compound

Participants

Reaction Steps

1-(6-Bromopyridin-2-yl)-N-methylmethanamine (115 mg, 0.571 mmol) was added to a stirred, room temperature mixture of 4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)benzoic acid (300 mg, 0.571 mmol), HATU (260 mg, 0.685 mmol, 1.2 equivalents) and DIPEA (498 μL, 2.85 mmol, 5 equivalents) in DMF (2.8 mL). The reaction was stirred at room temperature for 12 hours, and then diluted with EtOAc and partitioned with water. The aqueous layer was extracted with EtOAc (3×), and the combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by normal phase flash chromatography using silica gel (0-50% hexanes/ethyl acetate). The product was collected and concentrated in vacuo to afford the title compound (110 mg, 27%). LC-MS=608.2 & 610.2 (M-Boc+H)+.

Provenance & Evidence