1-Hydroxybenzotriazole → HCID 68809822, compound

Participants

Reaction Conditions

Reaction Steps

N-tert-BOC-4-oxo-L-proline (458 mg, 2 mmol), 3,3-difluoroazetidine hydrochloride (258 mg, 2 mmol) (prepared as described in WO 2000/47582), and DIPEA (0.35 mL, 2 mmol) were mixed in anhydrous methylene chloride (10 mL) and cooled to 0° C. HOBT (405 mg, 3 mmol) was then added in one portion followed by EDC hydrochloride (422 mg, 2.2 mmol). The resulting mixture was allowed to warm to RT and stirred overnight. Saturated sodium bicarbonate was added, the organic layer was separated, and the aqueous phase extracted with methylene chloride. The combined organic extracts were washed twice with brine, dried over magnesium sulfate, filtered, and concentrated. The crude product (570 mg) was triturated with hexanes:methylene chloride (10:1), filtered, and dried in a vacuum oven to afford 510 mg (84% yield) of the title product as a light orange powder. MS (m/z): 305.1 (MH+).

Provenance & Evidence