Nitrogen → [1-(2-Hydroxymethyl-oxazol-4-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester

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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-yl}-carbamic acid 2-chloro-benzyl ester (313 mg, 0.65 mmol) in dry THF (5.0 mL) was treated at 0° C. with TBAF (1.0 mL of a 1M solution in THF, 1.00 mmol). The reaction mixture was stirred at 0° C. for 30 min. Sat. aq. NH4Cl (10 mL) was added, the layers separated and the aq. layer extracted with EA (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (EA) gave the title compound as a pale yellow oil. TLC: rf (EA)=0.28. LC-MS-conditions 02: tR=0.84 min; [M+H]+=363.22.

Provenance & Evidence