Water → HCID 18948470, compound

Participants

Reaction Steps

2.3 g (14.7 mmole) of a sulfur trioxide/pyridine complex and 2.1 ml of triethylamine were added at room temperature to a solution of 1.96 g (4.91 mmole) of t-butyl 4-hydroxy-5-morpholino-2-(1-naphthylmethyl)pentanoate (prepared as described in Preparation 12) dissolved in 20 ml of anhydrous dimethyl sulfoxide. The mixture was stirred for 6 hours, allowed to stand overnight and then mixed with water, after which it was extracted with ethyl acetate. The organic layer was washed with water and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous magnesium sulfate. It was then concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: a 10: 90 by volume mixture of methanol and methylene chloride), to afford 1.30 g (66.7%) of the title compound as a pale brown oil.

Provenance & Evidence