Toluene → HCID 131725369, compound

Participants

Reaction Steps

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[N-(2-hydroxyethyl)-N-isopropyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (1.46 g, 2.79 mmol) (obtained as described in Reference Example 59(1)) in tetrahydrofuran (73 ml) were added diphenylphosphoryl azide (0.90 ml, 4.18 mmol), triphenylphosphine (1.10 g, 4.18 mmol), and a 40% solution of diethylazodicarboxylate in toluene (1.54 g, 4.18 mmol) in an ice bath under an atmosphere of nitrogen, and then the mixture was stirred for 3 hours under the same conditions. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using hexane:ethyl acetate (2:1) as the eluant to afford 1-{4-[N-(2-azidoethyl)-N-isopropyl-carbamoyl]-1,3-thiazol-2-yl}azetidine-3-t-butyldiphenylsilyloxyazetidine (1.38 g, yield 87%) as a pale yellow oil.

Provenance & Evidence