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-((5)-1-oxiranylmethoxy)-silane (commercial; 10.0 g, 53 mmol) in MeCN (160 mL) was added LiClO4 (16.9 g, 159 mmol). 6-amino-4H-benzo[1,4]oxazin-3-one (commercial; 8.72 g, 53.1 mmol) was added and the mixture was stirred at 50° C. for 6 h. The solvent was removed in vacuo and the residue was purified by FC (DCM/MeOH/NH4OH 1000:25:2 to 1000:100:2) to afford the title compound as a pale brown foam (10.24 g, 55% yield).

Provenance & Evidence