Acetic Acid → 3-(4-Benzyloxyphenyl)-2-diazo propionic acid methyl ester

Participants

Reaction Steps

A solution of 2.5 g (8.77 mmol) O-benzyl tyrosine methyl ester, 1.03 g (8.77 mmol) isoamyl nitrite, and 1.57 g (26.2 mmol) glacial acetic acid in chloroform (65 mL) was stirred and refluxed 15 min and then cooled to RT. The solution was concentrated to an oily residue, dissolved in EtOAc (100 mL), and washed with 5% NaHCO3. The organics were then dried (MgSO4), filtered, and concentrated to an oily residue which was chromatographed on silica gel using Hexane/EtOAc (1:1) to yield the title compound. 1H NMR (CDCl3) δ 7.43-7.31 (m, 5H) 7.14 (d, 2H, J=8.7) 6.90 (m, 2H) 5.03 (s, 2H) 3.76 (s, 3H) 3.56 (s, 2H).

Provenance & Evidence