Nitrogen → HCID 66928453, 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 4-[4-(2-chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-thiazole-2-carboxylic acid ethyl ester (912 mg, 2.17 mmol) in THF (20.0 mL) at −78° C. was treated with DiBAL (8.70 mL of a 1M solution in toluene, 8.70 mmol). The reaction mixture was stirred at −78° C. for 1 h, then allowed to reach rt before being quenched with Rochelle's salt (100 mL). The resulting mixture was stirred for 2 h at rt, extracted with EA (2×50 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (19:1 CH2Cl2-MeOH) gave the title compound as a yellow foam. TLC: rf (19:1 CH2Cl2-MeOH)=0.11. LC-MS-conditions 02: tR=0.83 min; [M+H]+=379.04.

Provenance & Evidence