Chloroacetic Acid → HCID 10385803, compound

Participants

Reaction Steps

3-Cyclopentyl-2-(6-mercaptopyridin-3-yl)-N-thiazol-2-ylpropionamide (EXAMPLE 66, 50 mg, 150 μmol) was added to a stirred suspension of NaH (12 mg of a 60% dispersion in mineral oil, 300 μmol) in anhydrous DMF (0.8 mL). After 5 min, a solution of chloroacetic acid (14 mg, 150 μmol) in anhydrous DMF (0.4 mL) was added. The reaction was stirred for 15 min, then more NaH (10 mg of a 60% dispersion in mineral oil, 250 μmol) and chloroacetic acid (14 mg, 150 μmol) were added. After 15 min, the reaction mixture was partitioned between EtOAc (10 mL) and saturated aqueous Na2CO3—H2O (1:1, 15 mL). The aqueous phase was acidified to pH 2.5 with 2M HCl, then the resulting precipitate was extracted into EtOAc (15 mL). The EtOAc solution was washed with brine (5 mL), dried (MgSO4), filtered, concentrated, and recrystallised (CH2Cl2—IH) to give the title compound: RTA=3.52 min; m/z (ES+)=392.2 [M+H]+.

Provenance & Evidence