Phenyl chloroformate → HCID 58055074, compound

Participants

Reaction Conditions

Reaction Steps

N-((2-aminothiazol-4-yl)methyl)-N,3,5-trimethylisoxazole-4-carboxamide hydrochloride (6.16 g, 20.34 mmol) was dissolved in pyridine (35 mL) and DMAP (150 mg, 5 mol %) was added. The solution was cooled to 0° C. and a solution of phenylchloroformate (2.55 mL, 3.18 g, 20.34 mmol) in tetrahydrofuran (35 mL) was added dropwise. The mixture was stirred overnight at room temperature and the volatiles were evaporated in vacuo. The residue was taken up in water/EtOAc. The organic phase was dried over MgSO4 and the volatiles were evaporated under reduced pressure. The material was crystallized from EtOAc/i-Pr2O to afford (4-{[methyl(3,5-dimethylisoxazole-4-carbonyl)-amino]-methyl}-thiazol-2-yl) carbamic acid phenyl ester (1.80 g) as a tan-colored solid (purity ˜85%). 1H NMR (CDCl3): δ 9.85 (bs, 1H), 7.45 (m, 2H), 7.25 (m, 2H), 7.20 (m, 2H), 6.80 (b, 1H), 4.75 (bs, 1H), 4.45 (bs, 1H), 3.00 (bs, 3H), 2.36 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence