Lithium Hydroxide → 3-[1-(3-tert-Butoxycarbonylamino-propyl)-piperidin-4-yl]-2-oxo-2,9-dihydro-3H-10-oxa-1,3,9-triaza-anthracene-7-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

1M of LiOH aqueous solution (4.5 mL, 3 equiv) and 3-[1-(3-tert-Butoxycarbonylamino-propyl)-piperidin-4-yl]-2-oxo-2,3,9,9a-tetrahydro-1H-10-oxa-1,3,9-triaza-anthracene-7-carboxylic acid methyl ester (5, 760 mg, 1.52 mmol, 1.0 equiv) was added to THF (5 mL), warmed up to 50° C. and stirred until LCMS showed no starting material left. The reaction solution was cooled to RT and extracted with EtOAc. The aqueous layer was acidified to pH 2 and the desired product was precipitated and filtered to yield 3-[1-(3-tert-Butoxycarbonylamino-propyl)-piperidin-4-yl]-2-oxo-2,9-dihydro-3H-10-oxa-1,3,9-triaza-anthracene-7-carboxylic acid (412 mg, 738 mg theoretical, 56%) as a light brown solid. For 6: C24H31N5O6, LCMS (EI) m/e 486(M++H).

Provenance & Evidence