Hydrochloric Acid → 6-Methoxy-2-Naphthoic Acid

Participants

Reaction Steps

A solution of LiOH.H2O (35.0 mg, 835 μmol, Eq: 5) in H2O (4 mL) was added to a solution of methyl 5-(((S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-5 (4H)-yl)methyl)-6-methoxy-2-naphthoate (110.5 mg, 167 μmol, Eq: 1.00) in THF (3 mL). After 18 h, the mixture was poured into 1 M HCl (20 mL) and extracted with EtOAc. The combined organic extracts were washed with H2O, brine, dried over Na2SO4 and concentrated. The residue was dissolved in MeCN/H2O, and lyophilized to afford 5-((S)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-5 (4H)-yl)methyl)-6-methoxy-2-naphthoic acid (95.2 mg, 88%) of white solid which was used without purification. MS m/z 648.2 (MH+)

Provenance & Evidence