Water → HCID 90308661, compound

Participants

Reaction Steps

A vial was charged with tert-butyl N-[(4aR,11bR)-10-[(5-chloro-3-methyl-pyridine-2-carbonyl)amino]-3,3,11b-trimethyl-4,4-dioxo-5,6-dihydro-4aH-[1]benzothiepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (90 mg, 0.130 mmol), THF (556 μl) water (185 μl) and MeOH (556 μl). Oxone (239 mg, 0.389 mmol) was added, and the mixture was stirred at RT for 72 h. Water and EtOAc were added, and the layers were separated. The organic portion was dried, filtered and concentrated. The crude material was dissolved in 1 mL DCM, and TFA (200 μl, 2.60 mmol) was added. The reaction was stirred at RT for 2 h. The solution was loaded onto an SCX column and washed with MeOH. The free base was eluted with ammonia/MeOH. The filtrate was concentrated, and the crude material was triturated in EtOAc, filtered, washed with EtOAc and dried to provide N-((4aR,11bR)-2-amino-3,3,11b-trimethyl-4,4,7,7-tetraoxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]thiepino[4,5-b][1,4]thiazin-10-yl)-5-chloro-3-methylpicolinamide (35 mg, 0.067 mmol, 51.3% yield) as a white solid. LC/MS (ESI+) m/z=525.1 (M+Na).

Provenance & Evidence