Benzyl chloroformate → HCID 18677363, compound

Participants

Reaction Steps

To a solution of the compound of Example 14 (1.9 g, 8.26 mmol) and NaHCO3 (2.08 g, 24.75 mmol) in water, (60 mL) was added drop-wise a solution of benzyl chloroformate (1.9 mL, 13.21 mmol) in dioxane (100 mL). The resulting mixture was stirred at room temperature for 4 hours, then was diluted with water (60 mL) and washed with ether (100 mL). The aqueous solution was acidified with 2 M KHSO4 and extracted with EtOAc (3×100 mL). The combined organic phases were washed with brine (200 mL), dried (Na2SO4), and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica gel (1:1 EtOAc/hexane, then 9:1 DCM/MeOH) to afford the title compound (1.6 g, 53%) as a pale yellow solid. 1H NMR (DMSO-d4) δ 2.24 (s, 2H), 4.64 (s, 2H), 5.13 (s, 2H), 7.20-7.45 (m, 5H), 9.22 (s, 1H), 9.29 (s, 1H). HPLC Rt 11.4 minutes (water/ACN/TFA, 5 to 75%, 0.1% TFA, 20 minutes).

Provenance & Evidence