Water → HCID 118574245, compound

Participants

Reaction Conditions

Reaction Steps

LiOH.H2O (9.1 mg, 217 μmol, Eq: 1.5) and H2O (1 mL) were added to a solution of (S)-methyl 3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-5-((2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylate (95 mg, 145 μmol, Eq: 1.00) in MeOH (4 mL). The mixture was heated to 50° C. After 2 h, LiOH.H2O (18 mg, 429 μmol, Eq: 2.95) was added and the temperature was increased to 60° C. After 4 h, the mixture was concentrated to a volume of approximately 1.5 mL. This mixture was acidified to pH 2 with 1 N HCl and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 filtered and concentrated to give a material that was purified by silica gel chromatography to afford (S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-5-((2-methoxynaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylic acid (31 mg, 37%) as an off-white foam.

Provenance & Evidence