Sodium Azide → HCID 86587220, compound

Participants

Reaction Conditions

Reaction Steps

(2S)-3-[4-(2-{4-[(tert-Butoxycarbonyl)amino]phenyl}ethoxy)phenyl]-2-ethoxypropyl methanesulfonate (described in Example 4a) (0.43 g, 0.87 mmole) was dissoved in dry DMF (5 ml). Sodium azide (0.23 g, 3.50 mmole) was added and the reaction mixture was heated to 80° C. and stirred overnight. The reaction was quenched with water and extracted with diethyl ether. The organic phase was washed with water, dried with magnesium sulfate and evaporated. The crude product was dissolved in dry diethyl ether and added to a solution of LAH (0.10 g, 2.62 mmole) in dry diethyl ether (50 ml). After one hour the reaction was quenched with water (0.5 ml), 5 M NaOH (1 ml) and water (0.5 ml) again. The mixture was refluxed for half an hour and the white precipitate was filtered off and the filtrate dried with magnesium sulfate and evaporated giving 0.63 g (72% yield) of the product.

Provenance & Evidence