Sodium borohydride → HCID 66744447, compound

Participants

Reaction Steps

A solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(4-oxocyclohexen-1-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (431 mg, 0.64 mmol) in MeOH (2 mL) was cooled in an ice water bath. Sodium boranuide (27 mg, 0.70 mmol) was added and the reaction mixture was stirred for 40 minutes at 0° C. upon which the ice bath was removed. After stirring at room temperature for 8 h, the reaction mixture was quenched with water and aq. NaHCO3 and diluted with EtOAc. The layers were separated and the aqueous layer was extracted once more with EtOAc. The combined organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by silica gel column chromatography using 0-40% EtOAc in DCM to yield tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(4-hydroxycyclohexen-1-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (126 mg, 41%). 1H NMR (400 MHz, DMSO-d6) δ 9.04 (s, 1H), 8.11 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.1 Hz, 2H), 7.01 (s, 1H), 4.81 (d, J=3.8 Hz, 1H), 4.49 (s, 2H), 3.93-3.86 (m, 1H), 2.83 (s, 5H), 2.64-2.53 (m, J=19.3 Hz, 2H), 1.97-1.90 (m, J=12.4 Hz, 1H), 1.71 (dd, J=14.0, 8.7 Hz, 1H), 1.45 (s, 3H), 1.36 (s, 6H), 1.26 (s, 18H); LC/MS m/z 579.9 [M+H]+.

Provenance & Evidence