Triethylamine → L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Participants

Reaction Steps

(S)-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)-3-phenylpropanoate (XVIII7): Following general procedure (F), after forming the intermediate, L-phenylalanine t-butyl ester hydrochloride (0.394 g, 1.53 mmol) and triethylamine (0.41 mL, 2.92 mmol) were added. After work-up and purification, 0.343 g of the title compound as a white foam solid was obtained (42% yield). mp: 62–66° C. MS: 607 (MH+). Anal. Calcd. for C29H25ClF4N2O5.0.5H2O: C, 58.49; H, 4.58; N, 4.55. Found: C, 58.47; H, 4.57; N, 4.28. 1H NMR (CDCl3): δ 1.46 (s, 9H), 3.13 (dd, J=14.0 Hz, 7.6 Hz, 1H), 3.30 (dd, J=14.0 Hz, 5.6 Hz, 1H), 3.34 (s, 3H), 4.80 (m, 1H), 6.74 (dd, J=8.8 Hz, 1.3 Hz, 1H), 7.20–7.27 (m, 6H), 7.36 (dd, J=8.7 Hz, 2.6 Hz, 1H), 7.41 (d, J=7.9 Hz, 1H), 7.78 (dd, J=2.5 Hz, 0.8 Hz, 1H), 8.57 (s, 1H), 8.68 (d, J=7.4 Hz, 1H). IR (KBr, cm−1): 3332, 2980, 1763, 1737, 1716, 1521, 1491, 1439, 1367, 1319, 1262, 1171, 1131, 1061.

Provenance & Evidence