Chlorine → 2-{(S)-2-[(E)-3-(5-chloro-2-tetrazol-1-yl-phenyl)-acryloylamino]-3-phenyl-propionylamino}-thiazole-5-carboxylic acid

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Reaction Steps

LiOH/THF/water hydrolysis of 2-{(S)-2-[(E)-3-(5-chloro-2-tetrazol-1-yl-phenyl)-acryloylamino]-3-phenyl-propionylamino}-thiazole-5-carboxylic acid ethyl ester (Example 19) afforded Example 21. HPLC purity: >98%. LCMS m/z 524.2 (M+H, chlorine isotope). 1H NMR (400 MHz, CD3OD) δ: 9.48 (s, 1H), 8.02 (s, 1H), 7.96 (d, J=2.3 Hz, 1H), 7.68 (dd, J=2.3 & 9.2 Hz, 1H), 7.56 (d, J=8.5 Hz, 1H), 7.31-7.19 (m, 5H), 7.10 (d, J=15.7 Hz, 1H), 6.75 (d, J=15.6 Hz, 1H), 4.9 (t, 1H), 3.30 (m, 1H), 3.11 (m, 1H) ppm. Analytical HPLC RT: 5.48 min (Method C, 8 min gradient).

Provenance & Evidence