Sodium borohydride → HCID 70823096, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of the compound from Step 6 (26 mg, 0.034 mmol) in EtOH (20 mL) was added BiCl3 (154 mg, 0.487 mmol) and then NaBH4 (363 mg, 9.61 mmol). The mixture was then warmed to 40° C. for 15 minutes. The black solids were then filtered off and washed with EtOH. 1N HCl was then added to quench the mixture at 0° C.; the EtOH was then removed in vacuo; and the pH was adjusted to ˜4. The mixture was then extracted with EtOAc (2×), dried over MgSO4, and the solvent was removed in vacuo to yield crude material which was purified by reverse phase chromatography using a 0-100% CH3CN/0.15% aqueous trifluoracetic acid gradient to yield the title compound. 1H NMR (500 MHz) (CD3OD) δ 8.99 (s, 1H), 8.56 (s, 1H), 8.15 (d, J=8.0 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 7.92 (app. t, J=7.2 Hz, 1H), 7.83 (app. t, J=7.6 Hz, 1H), 5.68 (q, J=10.0 Hz, 1H), 5.61 (app. t, J=3.2 Hz, 1H), 5.05 (app. t, J=8.8 Hz, 1H), 4.95-4.47 (m, 2H), 4.51 (dd, J=10.2 Hz, 6.8 Hz, 1H), 4.30 (d, J=10.4 Hz, 1H), 4.14 (dd, J=11.8 Hz, 3.6 Hz, 1H), 3.17 (m, 2H), 2.85 (m, 1H), 2.65 (m, 2H), 2.53 (m, 1H), 2.45 (q, J=8.4 Hz, 1H), 2.0-1.8 (m, 5H), 1.8-1.2 (m, 21H), 1.2-0.9 (m, 4H). LRMS ESI+ (M+H) 776.1, calcd for C41H54N5O8S: 776.3.

Provenance & Evidence