Triethylamine → (S)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-oxazolidine-3-carboxylic acid benzyl ester

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Reaction Steps

(S)-Oxazolidine-3,4-dicarboxylic acid 3-benzyl ester (51.3 mg, 0.20 mmol) was dissolved in DMF (1.5 mL). Triethylamine (56 μL, 0.40 mmol) and pentafluorophenyl trifluoroacetate (35 μL, 0.20 mmol) were added, and the reaction was allowed to stir at ambient temperature for 25 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide trifluoroacetic acid salt (148.8 mg, 0.40 mmol) was added, and the reaction was stirred at ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product. Yield 10.2 mg. MS: 493.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.52-0.74 (m, 4H), 4.05-4.37 (m, 2H), 4.58-4.69 (m, 1H), 4.90-5.17 (m, 4H), 7.00-7.45 (m, 4H), 7.72-7.98 (m, 5H), 8.37-8.48 (m, 1H), 12.48-12.51 (s, 1H).

Provenance & Evidence