6-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one → (RS)-6-[4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-butylamino]-4H-benzo[1,4]thiazin-3-one

Participants

Reaction Steps

A solution of (RS)-tert-butyl-dimethyl-(2-oxiranyl-ethoxy)-silane (4 g, 20 mmol; prepared according to Heterocycles (1987), 25(1), 329-32) and 6-amino-4H-benzo[1,4]thiazin-3-one (4 g, 20 mmol) in EtOH/water 9:1 (140 mL) was heated at 80° C. for 2 days. The mixture was concentrated under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000:50:4) to afford the title intermediate as a brown oil (2.2 g, 29% yield).

Provenance & Evidence