Reaction #502117

Reaction equation

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

NaHCO3

tert-butyl bromoacetate

→

title compound

((tert-Butyl)oxycarbonyl)methyl(2S)-2-(6-methoxy(2-naphthyl))propanoate

Solvents

DMF

Conditions

Workup

1. 1
   Otherthe solvent was evaporated under high vacuo
2. 2
   workup.ADDITIONThe residue was then diluted with CH2Cl2
3. 3
   Otherthe solvent removed by filtration
4. 4
   Otherthe residue was recrystallized from a mixture of CH2Cl2/EtOAc/Hex

Procedure

A mixture of (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (naproxen, 3 g, 13.0 mmol), NaHCO3 (1.4 g, 16.7 mmol) and tert-butyl bromoacetate (5.08 g, 26.0 mmol) in DMF (30 mL) was stirred at room temperature for 2 days and the solvent was evaporated under high vacuo. The residue was then diluted with CH2Cl2, the solvent removed by filtration and the residue was recrystallized from a mixture of CH2Cl2/EtOAc/Hex to give the title compound as a white solid in quantitative yield. Mp 85-86° C. 1H NMR (300 MHz, CDCl3) δ 7.69-7.70 (m, 3H), 7.43 (dd, J=1.6 and 8.6 Hz, 1H), 7.10-7.15 (m, 2H), 4.47 (ABq, JAB=15.7 Hz, ΔvAB=40.7 Hz, 2H), 3.97 (q, J=7.2 Hz, 1H), 3.90 (s, 3H), 1.63 (d, J=7.2 Hz, 3H), 1.42 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 174.2, 166.9, 157.8, 135.4, 133.9, 129.5, 129.1, 127.3, 126.5, 126.3, 119.1, 105.8, 82.5, 61.7, 55.5, 45.3, 28.1, 18.8. Mass spectrum (API-TIS) m/z 345 (MH+), 362 (MNH4+).

Source