Nitrogen → (5-(Methoxymethyl)thiazol-2-yl)methyl methanesulfonate

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 (5-(methoxymethyl)thiazol-2-yl)methanol (201 mg, 1.26 mmol) in dry CH2Cl2 (10.0 mL) was treated at 0° C. with Et3N (0.23 mL, 1.63 mmol) followed by DMAP (15.6 mg, 0.13 mmol) and Ms-Cl (0.13 mL, 1.59 mmol). After stirring at 0° C. for 30 min, the reaction was quenched with water (10 mL). The org. layer was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give 300 mg of crude (5-(methoxymethyl)thiazol-2-yl)methyl methanesulfonate as an orange oil. LC-MS-conditions 07: tR=0.59 min, [M+H]+=238.07. A solution of this crude material (300 mg) in DMF (3.0 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (1.50 g of a 9.6% solution in DMF, 1.26 mmol) in DMF (3.0 mL) pre-treated for 30 min with DIPEA (0.43 mL, 2.53 mmol) and the reaction mixture was stirred for 24 h at 50° C. Water (10 mL), followed by EA (10 mL) was added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:1 hept-EA)=0.29. LC-MS-conditions 07: tR=0.70 min, [M+H]+=255.85.

Provenance & Evidence