Triphenylphosphine → methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate

Participants

Reaction Steps

To a solution of methyl (R)-8-hydroxy-4-[3-(3-pyridyl)propyl]octanoate (1.09 g 3.7 mmol), N-t-butoxy-carbonyl-p-chlorophenylsulfonamide (1.52 g, 5.2 mmol) and triphenylphosphine (1.92 g, 7.3 mmol) in methylene chloride (17 ml) is added dropwise diethyl azodicarboxylate (0.82 ml, 5.2 mmol). The reaction mixture is allowed to stir or 1 hour and the solvent is evaporated. The residue is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane to obtain methyl (R)-8-[N-t-butoxy-carbonyl-p-chlorophenylsulfonamido]-4-[3-(3-pyridyl)propyl]octanoate; IR (CH2Cl2): 1730, 1356, 1154 cm- 1.

Provenance & Evidence