Methanol → methyl 5-(((S)-3-((S)-2-(tert-butoxycarbonyl (methyl)amino)propanamido)-4-oxo-3,4-dihydrobenzo[b][1,4]oxazepin-5(2H)-yl)methyl)-6-methoxy-2-naphthoate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl (S)-1-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (1.8 g, 2.94 mmol, Eq: 1.00), Pd(OAc)2 (33.0 mg, 147 μmol, Eq: 0.05) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (170 mg, 294 μmol, Eq: 0.10) in a microwave tube was evacuated and purged with N2. MeOH (1.43 g, 1.8 mL, 44.5 mmol, Eq: 15.1) and TEA were added, the vessel was purged with CO and heated at 70° C. under CO overnight. The mixture was concentrated and the residue was purified by silica gel chromatography to afford methyl 5-(((S)-3-((S)-2-(tert-butoxycarbonyl (methyl)amino)propanamido)-4-oxo-3,4-dihydrobenzo[b][1,4]oxazepin-5(2H)-yl)methyl)-6-methoxy-2-naphthoate (1.24 g, 2.1 mmol, 71.3%).

Provenance & Evidence