Nitrogen → HCID 57336781, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(2-((4-(2-methyl-5-(m-tolyl)oxazole-4-carboxamido)-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)cyclopropyl pivalate (70 mg, 0.14 mmol) in THF (1.4 mL) was treated at 0° C. with DiBAL-H (0.7 mL of a 1M solution in THF, 0.70 mmol) and the resulting solution was stirred for 3.5 h at 0° C. The reaction mixture was poured onto a Rochelle's salt aq. solution (14 mL) and the mixture was vigorously stirred for 2 h at rt. The two layers were separated and the aq. phase was extracted with EA (14 mL). The combined org. layers were dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (4:6 hept-EA) gave the title compound as a yellow oil: TLC: rf (4:6 hept-EA)=0.30. LC-MS-conditions 06: tR=0.86 min, [M+H]+=421.22

Provenance & Evidence