(S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione → (S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

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Reaction Steps

(S)-5-(2-Phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (17) was prepared according to the same procedure for compound 10, except using compound 16, and purified with ether to afford 715 mg (63%) of 17 as a yellow solid, mp 173.2-174.5° C. 1H NMR (300 MHz, DMSO) δ 11.48 (s, 1H), 7.98 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.77 (s, 1H), 7.27 (m, 2H), 7.10 (d, J=8.1 Hz, 1H), 6.91 (d, J=7.8 Hz, 3H), 4.20-4.02 (m, 3H), 3.70 (m, 1H), 3.55 (m, 1H), 2.22 (m, 1H), 2.02 (m, 1H). LRMS (FAB) m/e: 373.0 (M+H, 100). Anal. Calcd for C18H16N2O5S.0.5H2O: C, 56.68, H, 4.49; N, 7.34. Found: C, 56.96, H, 4.39; N, 7.30.

Provenance & Evidence