Hydride → HCID 118060319, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl (allyl{[allyl(tert-butoxycarbonyl)amino]sulfonyl}amino)acetate (1.11 g, 3.05 mmol) in dichloromethane (15 mL) at −78° C. under N2 was treated with 1.0 M diisobutylaluminun hydride in dichloromethane (3.66 mL, 3.66 mmol, 1.2 equiv.). The reaction mixture was stirred at −78° C. for 1 h and then quenched with methanol (1.5 mL) and treated with a saturated solution of sodium potassium tartrate (65 mL). This solution was stirred at room temperature overnight. The aqueous layer was then extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was washed with brine, dried over sodium sulfate, filtered, and concentrated to give the desired product (0.62 g, 64%) as a crude thick colorless oil, which was used in subsequent reaction without further purification. 1H NMR (300 MHz, DMSO-d6) δ 9.45 (s, 1H), 5.76 (m, 2H), 5.18 (m, 4H), 4.15 (m, 4H), 3.72 (m, 2H), 1.43 (s, 9H).

Provenance & Evidence