6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one → 6-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propylamino]-4H-benzo[1,4]oxazin-3-one

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl-dimethyl-((S)-1-oxiranylmethoxy)-silane (commercial; 4.25 g, 22.6 mmol) in MeCN (70 mL) was added LiClO4 (7.20 g, 3 eq.). 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 3.70 g, 1 eq.) was then added and the mixture was stirred at 50° C. for 6 h. The solvent was removed under reduced pressure and the residue was purified by CC (DCM/MeOH/NH4OH 1000/25/2) to afford the title intermediate as a pale brown foam (5.25 g, 66% yield).

Provenance & Evidence