Toluene → HCID 22243019, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[N-methyl-N-(2-hydroxyethyl)carbamoyl]-1,3-thiazol-2-yl}azetidine (997.5 mg, 2.0 mmol) (obtained as described in Reference Example 58(1)) in tetrahydrofuran (50 ml) were added diphenylphosphoryl azide (0.65 ml, 3.02 mmol), triphenylphosphine (793 mg, 3.02 mmol), and a 40% solution of diethylazodicarboxylate in toluene (1.12 g, 3.04 mmol) in an ice bath under an atmosphere of nitrogen, and the mixture was stirred overnight under the same conditions. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using toluene:ethyl acetate (1:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-{4-[N-(2-azidoethyl)-N-methyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (1.05 g, yield 100%) as a colorless and transparent syrup.

Provenance & Evidence