L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 67496344, compound

Participants

Reaction Steps

The 6-bromoindoline (1050 mg, 5.30 mmol), N—BOC-phenylalanine (1.41 g, 5.30 mmol), N-ethyl-N-isopropylpropan-2-amine (2.02 ml, 12.2 mmol) and 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (2.41 g, 6.36 mmol) (HBTU) were dissolved in DMF. The reaction mixture was stirred for 2.5 days. The reaction was diluted with water and then extracted with ethyl acetate (2×150 mL). The combined organic layers were washed with 1M lithium chloride solution (2×70 mL) and brine (1×70 mL) and dried over magnesium sulfate. The crude product was then recrystallyzed using ethyl acetate:hexanes to give (S)-tert-butyl 1-(6-bromoindolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate (1.01 g, 42.8% yield). MS ESI (pos.) m/e: 445.1 (M+H).

Provenance & Evidence