Nitric Acid → HCID 52913599, compound

Participants

Reaction Steps

To a stirred solution of acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester (Example 5, 104 mg, 2 mmol) in dichloromethane (25 ml) was added HNO3 (6% aqueous solution, 5.6 ml, 3.8 mmol) in a drop wise fashion, followed by the addition of tetrabutyl ammonium bromide (100 mg). The reaction mixture was stirred at room temperature until the complete conversion. The reaction mixture was diluted with DCM, washed with water, brine, concentrated and purified by silica gel chromatography to give 1.2 g of acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-hydroxy-3-nitro-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester.

Provenance & Evidence