Diisopropylethylamine → HCID 69675210, compound

Participants

Reaction Steps

Methyl (S)-3-methyl-1-oxo-1-((S)-8-(5-(4-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)butan-2-ylcarbamate as 3HCl salt (200 mg, 0.24 mmol), (R)-2-(methoxycarbonylamino)-2-phenylacetic acid (60 mg, 0.288 mmol), and COMU (154 mg, 0.36 mmol) were all weighed out in a scintillation vial and anhydrous N,N-dimethylformamide (2.4 mL) was added and without stirring to this mixture was then added DIPEA (124 mg, 0.96 mmol) and the mixture was sonicated to dissolve all the reactants as quickly as possible. The mixture was then stirred for 2 h at room temperature. The crude mixture was diluted with EtOAc and washed with brine, 10% Na2CO3, brine and the organic layer was dried over MgSO4. The filtrate was concentrated down and the residue was purified by normal phase column chromatography (5% MeOH/DCM). MS (ESI) m/z 881.84 [M+H]+. (95 mg, 45%).

Provenance & Evidence