4-Aminophenylacetic acid → HCID 56923945, compound

Participants

Reaction Steps

4-aminophenyl acetic acid (204 mg, 1.35 mmol) in a 10 mL flask was dissolved in a mixture of 10% aqueous sodium bicarbonate (0.29 mL) and tetrahydrofuran (2.3 mL) then cooled in an ice/water bath. 9-fluorenylmethyl chloroformate (367 mg, 1.42 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 284 mg of product (56% yield). Mass spectrum (M+Na)+ calcd for C23H19NO4, 396.1. found, 396.1.

Provenance & Evidence