Triethylamine → HCID 58864454, compound

Reaction equation

C[Si](I)(C)C.[CH3:6][O:7][C:8](=[O:33])[C@H:9]([NH:22]C(OCC1C=CC=CC=1)=O)[CH2:10][C:11]1[C:20]([Br:21])=[CH:19][C:14]2[NH:15][C:16](=[O:18])[O:17][C:13]=2[CH:12]=1.C(N(CC)CC)C>C(#N)C>[CH3:6][O:7][C:8](=[O:33])[C@H:9]([NH2:22])[CH2:10][C:11]1[C:20]([Br:21])=[CH:19][C:14]2[NH:15][C:16](=[O:18])[O:17][C:13]=2[CH:12]=1

Participants

Procedure

Trimethylsilyliodide (73 mL, 0.73 mmol) was added to a solution of azotropically dried (R)-2-benzyloxycarbonylamino-3-(5-bromo-2-oxo-2,3-dihydro-benzooxazol-6-yl)-propionic acid methyl ester (146 mg, 0.33 mmol) in acetonitrile (10 mL) at room temperature, and the resulting mixture was stirred at room temperature for 2 h. Triethylamine (0.12 mL) was added and the mixture was stirred at room temperature for 15 min. The solvents were removed in vacuo, and the residue was extracted with ethyl acetate. The combined organics were washed with sodium bicarbonate and brine, dried over sodium sulfate and filtered. Solvents were removed and the residue was used directly in the next step. Mass spec. 315.10 (MH)+.