9-Fluorenylmethyl chloroformate → HCID 56923947, compound

Participants

Reaction Steps

3-(4-aminophenyl)propionic acid (250 mg, 1.5 mmol) in a 10 mL flask was dissolved in a mixture of 10% aqueous sodium bicarbonate (0.32 mL) and tetrahydrofuran (2.2 mL) then cooled in an ice/water bath. 9-fluorenylmethyl chloroformate (422 mg, 1.5 mmol) was added in small portions over 3 min. After 4 h the cooling bath was removed. After additional 4 h at room temperature, the reaction was extracted with deionized water (2 mL) and ethyl ether (2 mL) and the aqueous layer was brought to pH 4 with dilute HCl and placed in a refrigerator. After 1 h solid was collected by vacuum filtration and washed with deionized water then dried under vacuum to give 470 mg of product (80% yield). Mass spectrum (M+Na)+ calcd for C24H21NO4, 400.1. found 410.0.

Provenance & Evidence