Methylamine → HCID 86670469, compound

Participants

Reaction Steps

Methylamine (5.71 mL of a 2M THF solution, 11.4 mmol) was added to a stirred, room temperature solution of 4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)benzoic acid (2.00 g, 3.80 mmol), HATU (1.736 g, 4.56 mmol, 1.2 equivalents) and DIPEA (3.32 mL, 19.0 mmol, 5 equivalents) in DMF (7.8 mL). The reaction was stirred at room temperature for 12 hours, after which the mixture was diluted with EtOAc and partitioned with water. The aqueous layer was extracted with EtOAc (3×), and the combined organic layers 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 fractions were collected and concentrated in vacuo to afford the title compound as a white solid (1.20 g, 59%). LC-MS=561.2 (M+Na)+.

Provenance & Evidence