HCID 53904716, compound → HCID 54138363, compound

Participants

Reaction Steps

A solution of methyl (R)-4-(1-acetylaminoethyl)-3-azidobenzoate (1.6 g) in 2N hydrochloric acid (25 ml) was refluxed under heating for 8 hours. After the reaction, the mixture was concentrated under reduced pressure, and boiled with toluene to give crude (R)-3-azido-4-(1-aminoethyl)benzoic acid (1.7 g). Then, the mixture was added to a solution of sodium hydroxide (0.85 g) in water (25 ml). Benzyloxycarbonyl chloride (1.56 g) was dropwise added, and the mixture was stirred at room temperature for 5 hours. After the reaction, the solution was adjusted to have pH 4 with conc. hydrochloric acid. The mixture was extracted with chloroform, washed with water, and dried. The solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=30:1) to give 1.6 g of pale-yellow (R)-3-azido-4-(1-benzyloxycarbonylaminoethyl)benzoic acid.

Provenance & Evidence