Tert-butyl 2-[(2-acetamido-1,3-thiazol-5-yl)sulfanyl]acetate → [[2-(Acetylamino)-5-thiazolyl]thio]acetic acid

Participants

Reaction Steps

A solution of [[2-(acetylamino)-5-thiazolyl]thio]acetic acid 1,1-dimethylethyl ester (4.32 g, 15 mmol) in methylene chloride (30 mL) and trifluoroacetic acid (20 mL) was stirred at rt overnight and concentrated in vacuo. To the residue was added ethyl ether (50 mL). The precipitated solid was collected, washed with ethyl ether and dried to afford the desired product (3.38 g, 97%) as a solid, mp 210° C. 1H NMR (CD3OD) δ7.48 (s, 1 H), 3.47 (s, 2 H), 2.20 (s, 3 H) ppm; MS m/e 231 (M-H)- ; HPLC (Column: Zorbax Rapid resolution C-18; flow rate: 2.5 mL/min; solvent system: 0-100% B in 8 min. Solvent A: 10% MeOH-90% water-0.2%H3PO4 ; Solvent B: 90% MeOH-10% Water-0.2% H3PO4 ; UV: 254 nm): retention time 4.32 min.

Provenance & Evidence