Benzyl chloroformate → HCID 18677361, compound

Participants

Reaction Steps

To a solution of the compound of Example 5 (Step G) (5.0 g, 0.025 mol) and NaHCO3 (9.4 g, 0.112 mol) in water (180 mL), was added drop-wise a solution of benzylchloroformate (6.0 mL, 0.042 mol) in dioxane (300 mL). The resulting mixture was stirred at room temperature for 4 hours, diluted with water (200 mL), and washed with ether (200 mL). The aqueous phase was acidified with aqueous 2M KHSO4 and extracted with EtOAc (3×300 mL). The combined organic phases were washed with brine (400 mL), dried (Na2SO4), and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica gel to afford the title compound (7.35 g, 90%) as a pale brown solid. 1H NMR (DMSO-d4 ) δ2.15 (s, 3H), 4.3 (br s, 1H), 4.73 (s, 2H), 5.12 (s, 2H), 6.76 (s, 1H), 7.20-7.50 (m, 5H), 9.7 (br s, 1H), 10.0 (br s, 1H). HPLC Rt 8.10 minutes (water/ACN/TFA, 5 to 75%, 0.1% TFA, 20 minutes).

Provenance & Evidence