Nitrogen → {1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-yl}-carbamic acid 2-chloro-benzyl ester

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-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-1H-pyrazol-4-ylamine (347 mg, 1.12 mmol) in CH2Cl2 (5.0 mL) was treated with DIPEA (0.31 mL, 1.78 mmol) followed by 2-chlorobenzylchloroformate (0.23 mL, 1.45 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and water (5.0 mL) was added. The layers were separated and the aq. layer extracted with CH2Cl2 (2×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (9:1 to 1:1 hept-EA) gave the title compound as an orange oil. TLC: rf (1:1 hept-EA)=0.27. LC-MS-conditions 02: tR=1.13 min; [M+H]+=476.95.

Provenance & Evidence