3-Aminoazetidine, 3-BOC protected → HCID 57937374, compound

Participants

Reaction Steps

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazole-5-sulfonyl chloride (0.41 g, 1.0 mmol), tert-butyl azetidin-3-ylcarbamate (0.17 g, 1.0 mmol) and DMAP (0.37 g, 3.0 mmol) in MeCN (20 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 0.40 g (74%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.33 (s, 9 H), 1.48-1.62 (m, 2 H), 1.64 (s, 9 H), 1.67-1.87 (m, 4 H), 1.98-2.15 (m, 2 H), 2.19-2.35 (m, 1 H), 3.62 (t, J=7.03 Hz, 2 H), 3.96 (t, J=8.11 Hz, 2 H), 4.05-4.16 (m, 1 H), 4.51 (d, J=7.42 Hz, 2 H), 7.86 (dd, J=9.18, 1.17 Hz, 1 H), 7.98 (d, J=8.79 Hz, 1 H), 8.14 (d, J=1.56 Hz, 1 H); MS (ESI) (M+H)+=541.3; Anal. Calcd for C26H38F2N4O4S+1.00 TFA+0.20 EtOAc (674.72): C, 51.62; H, 6.07; N, 8.30. Found: C, 51.73; H, 5.94; N, 8.27.

Provenance & Evidence