Iodoacetamide → HCID 86583569, compound

Participants

Reaction Conditions

Reaction Steps

The ethyl (RS)-(4-cyano-phenylamino)-(4-isopropoxy-5-isopropyl-2-methyl-phenyl)-acetate (921 mg, 2.34 mmol) obtained in Example 254.2 was dissolved in CH2Cl2 and cooled to −78° C. A 1M solution of BBr3 in CH2Cl2 (9.4 ml, 9.4 mmol) was slowly added dropwise. After 15 min. the reaction mixture was left to warm to 0° C. and was stirred for 1.5 h. at 0° C. Ice-water (30 ml) was added and the mixture was stirred for 10 min. at 0° C. The organic phase was separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried, filtered and concentrated. The crude product was dissolved in acetone, Cs2CO3 (918 mg, 2.76 mmol) and iodoacetamide (447 mg, 2.41 mmol) were added and the mixture was stirred for 6 h. at room temperature. A dilute aqueous solution of KHSO4 was added and the mixture was extracted with CH2Cl2. The organic phase was dried, filtered and concentrated, and the residue was purified by chromatography (SiO2, hexane/EtOAc 1:1=>1:2). There were obtained 704 mg, (73%) of ethyl (RS)-(4-cyano-phenylamino)-(4-carbamoylmethoxy-5-isopropyl-2-methyl-phenyl)-acetate as a colorless foam.

Provenance & Evidence