Reaktion #1462913

Reaktionsgleichung

triethylamine

(S)-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)propanoate

→

(L)-Alanine-t-butyl ester hydrochloride

Reaktionsbedingungen

Vorschrift

(S)-tert-butyl 2-((S)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indoline-1-carboxamido)propanoate (XVIII1): Following general procedure (F), after forming the intermediate, (L)-Alanine-t-butyl ester hydrochloride (0.252 g, 1.39 mmol) and triethylamine (0.39 mL, 2.78 mmol) were added. After work-up and purification, 0.38 g of the title compound was obtained as a white foam solid (52% yield). mp: 62–64° C. MS: 531 (MH+). Anal. Calcd. for C24H23ClF4N2O5: C, 54.30; H, 4.37; N, 5.28. Found: C, 54.37; H, 4.38; N, 5.16. 1H NMR (CDCl3): δ 1.51 (s, 9H), 1.56 (d, J=6.9 Hz, 3H), 3.54 (s, 3H), 4.52 (m, 1H), 6.77 (dd, J=8.8 Hz, 1.4 Hz, 1H), 7.25 (m, 1H), 7.36 (dd, J=8.7 Hz, 2.6 Hz, 1H), 7.43 (d, J=7.9 Hz, 1H), 7.80 (dd, J=2.5 Hz, 0.9 Hz, 1H), 8.6 (m, 1H), 8.76 (d, J=6.8 Hz, 1H). IR (KBr, cm−1): 3338, 2983, 1765, 1737, 1716, 1520, 1490, 1439, 1319, 1262, 1172, 1130.

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