Acetoxyacetyl chloride → HCID 10136608, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(4-amino-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (prepared in Example 3, 105 mg, 0.33 mmol) in tetrahydrofuran (10 mL) was treated with N,N-diisopropylethylamine (0.068 mL, 0.40 mmol) and acetoxy acetyl chloride (0.03 mL, 0.33 mmol). The reaction mixture was stirred at 25° C. for 5 h. At this time, the reaction was concentrated in vacuo. High pressure liquid chromatography (Chromegasphere SI-60, 10 μM, 60 Å, 25 cm×23 cm ID, 50/50 heptane/ethyl acetate) afforded acetic acid {4-[2-cyclopentyl-1-(thiazol-2-ylcarbamoyl)-ethyl]-phenylcarbamoyl}-methyl ester (31.4 mg, 22.7%) as a white solid: mp 90-95° C.; EI-HRMS m/e calcd for C21H25N3O4S (M+) 415.1565, found 415.1567.

Provenance & Evidence