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

Temperature

0 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (2-(methoxymethyl)thiazol-5-yl)methanol (319 mg, 2.00 mmol) in dry CH2Cl2 (15.0 mL) was treated at 0° C. with Et3N (0.36 mL, 2.59 mmol) followed by DMAP (25 mg, 0.20 mmol) and Ms-Cl (0.20 mL, 2.53 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 469 mg (quant.) of crude (2-(methoxymethyl)thiazol-5-yl)methyl methanesulfonate as an yellow oil: TLC: rf (1:4 hept-EA)=0.39. A solution of this crude material (469 mg) in DMF (4.5 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (2.35 g of a 9.6% solution in DMF, 1.98 mmol) in DMF (4.5 mL) pre-treated for 30 min with DIPEA (0.68 mL, 3.96 mmol) and the reaction mixture was stirred for 4 days at 50° C. Water (10 mL), followed by EA (10 mL) were 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)=0.33. LC-MS-conditions 07: tR=0.72 min, [M+H]+=255.95.

1. customthe reaction was quenched with water (10 mL)
2. dry with materiallayer was dried over Na2SO4
3. filtrationfiltered
4. customthe solvents were removed under reduced pressure

ORD record

ord-7cdd67870cf64c169e71fe3933926a9a

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846733B2