Dimethylformamide → HCID 118071210, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Intermediate 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (273 mg, 1.47 mmol) in toluene (6 mL) was added TEA (0.472 ml, 3.39 mmol) followed by DPPA (0.22 ml, 1.0 mmol) and the mixture was stirred at 90° C. for 1 h. The reaction mixture was cooled to RT and a solution of Intermediate 185B (200 mg, 0.679 mmol) in DMF (2 mL) was added and stirring continued at RT for 16 h. The reaction was quenched with a 10% aq. solution of NaHCO3, the organic layer was separated, dried over sodium sulfate, and concentrated. The crude product was purified by silica gel chromatography (4 g REDISEP® column, eluting with 5% MeOH in CHCl3). Fractions containing the product were combined and evaporated to afford Intermediate 339A as a buff colored solid (250 mg, 75% yield) MS(ES): m/z=493.

Provenance & Evidence